100 named reactions with examples of total syntheses which utilized these reactions, with reaction conditions. with included references for each syntheses.
The Mannich reaction involves the condensation of an enolizable carbonyl compound, an amine or ammonia, and formaldehyde to form an aminomethyl derivative known as a Mannich base. Ketones are most commonly used as the carbonyl compound. The reaction proceeds via the generation of an imine intermediate from the carbonyl compound and amine, which then reacts with formaldehyde to form the Mannich base. Mannich bases have applications in synthesizing natural products like alkaloids and building ring systems.
The Barton reaction involves the photolysis of an alkyl nitrite to form a δ-nitroso alcohol which can dimerize or form an oxime. Sir Derek Barton discovered this reaction in 1960 and was awarded the Nobel Prize in Chemistry in 1969 for his work, including understanding the Barton Reaction. The reaction mechanism involves homolytic cleavage of the RO-NO bond, followed by δ-hydrogen abstraction, radical recombination, and tautomerization to form an oxime. An example provided is the Barton reaction of butyl nitrite to form a δ-nitroso butanol that can then dimerize or form an oxime. Applications include the synthesis of natural products like hormones and alkaloids.
This powerpoint is about the mannich reaction i.e.,formation of a beta amino ketone...
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CHE-MYSTERY
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The document provides information about various organic chemistry reactions including the Baeyer-Villiger oxidation, Shapiro reaction, Suzuki coupling, ozonolysis, and Michael reaction. It discusses the reaction mechanisms, applications in synthesis, and key steps for each reaction. Examples are given of uses in synthesizing natural products and complex molecules.
E1 &E2 mechanism, sandmeyer and benzyne mechanismlsk1976
The document discusses the Sandmeyer reaction, which is a type of radical-nucleophilic aromatic substitution reaction that replaces an amino group on an aromatic ring with different substituents. During the reaction, the amino group is converted to a diazonium salt that can then be transformed into various functional groups using a catalyst. It also describes the reaction of halobenzenes with potassium amide in liquid ammonia to yield aniline, which proceeds through an elimination-addition mechanism involving the elimination of an alpha hydrogen and addition of an amide anion to form an intermediate benzyne structure.
The document discusses the Ugi reaction, a multi-component reaction first reported in 1959 by Prof. Ivar Karl Ugi. The Ugi reaction involves a ketone or aldehyde, an amine, an isocyanide, and a carboxylic acid to form a bis-amide derivative. It is exothermic, fast, and high-yielding. By varying the substituents, large chemical libraries can be synthesized from a single reaction. The Ugi reaction is used in combinatorial chemistry and drug development, such as for the HIV drug Crixivan.
The McMurry coupling reaction is a versatile titanium-mediated process for forming carbon-carbon bonds via the reductive coupling of carbonyl compounds to produce alkenes. Key features of the reaction include the use of low-valent titanium complexes to couple aldehydes and ketones, most commonly prepared by reducing TiCl3 with Zn-Cu. The reaction can form sterically hindered and strained alkenes in high yields. While it lacks stereoselectivity, the McMurry coupling has been used in the synthesis of many natural products due to its ability to form carbon-carbon bonds and macrocyclic rings.
The Mannich reaction involves the condensation of an enolizable carbonyl compound, an amine or ammonia, and formaldehyde to form an aminomethyl derivative known as a Mannich base. Ketones are most commonly used as the carbonyl compound. The reaction proceeds via the generation of an imine intermediate from the carbonyl compound and amine, which then reacts with formaldehyde to form the Mannich base. Mannich bases have applications in synthesizing natural products like alkaloids and building ring systems.
The Barton reaction involves the photolysis of an alkyl nitrite to form a δ-nitroso alcohol which can dimerize or form an oxime. Sir Derek Barton discovered this reaction in 1960 and was awarded the Nobel Prize in Chemistry in 1969 for his work, including understanding the Barton Reaction. The reaction mechanism involves homolytic cleavage of the RO-NO bond, followed by δ-hydrogen abstraction, radical recombination, and tautomerization to form an oxime. An example provided is the Barton reaction of butyl nitrite to form a δ-nitroso butanol that can then dimerize or form an oxime. Applications include the synthesis of natural products like hormones and alkaloids.
This powerpoint is about the mannich reaction i.e.,formation of a beta amino ketone...
It's helpful for JAM/NET/GATE/Polytechnic trb aspirants..
Follow me on youtube
CHE-MYSTERY
Subscribe and press bell button for notification
The document provides information about various organic chemistry reactions including the Baeyer-Villiger oxidation, Shapiro reaction, Suzuki coupling, ozonolysis, and Michael reaction. It discusses the reaction mechanisms, applications in synthesis, and key steps for each reaction. Examples are given of uses in synthesizing natural products and complex molecules.
E1 &E2 mechanism, sandmeyer and benzyne mechanismlsk1976
The document discusses the Sandmeyer reaction, which is a type of radical-nucleophilic aromatic substitution reaction that replaces an amino group on an aromatic ring with different substituents. During the reaction, the amino group is converted to a diazonium salt that can then be transformed into various functional groups using a catalyst. It also describes the reaction of halobenzenes with potassium amide in liquid ammonia to yield aniline, which proceeds through an elimination-addition mechanism involving the elimination of an alpha hydrogen and addition of an amide anion to form an intermediate benzyne structure.
The document discusses the Ugi reaction, a multi-component reaction first reported in 1959 by Prof. Ivar Karl Ugi. The Ugi reaction involves a ketone or aldehyde, an amine, an isocyanide, and a carboxylic acid to form a bis-amide derivative. It is exothermic, fast, and high-yielding. By varying the substituents, large chemical libraries can be synthesized from a single reaction. The Ugi reaction is used in combinatorial chemistry and drug development, such as for the HIV drug Crixivan.
The McMurry coupling reaction is a versatile titanium-mediated process for forming carbon-carbon bonds via the reductive coupling of carbonyl compounds to produce alkenes. Key features of the reaction include the use of low-valent titanium complexes to couple aldehydes and ketones, most commonly prepared by reducing TiCl3 with Zn-Cu. The reaction can form sterically hindered and strained alkenes in high yields. While it lacks stereoselectivity, the McMurry coupling has been used in the synthesis of many natural products due to its ability to form carbon-carbon bonds and macrocyclic rings.
The document summarizes the pinacol-pinacolone rearrangement, which involves the conversion of a vicinal diol to a ketone or aldehyde in the presence of an acid. It was first described by German chemist William Rudolph Fittig in 1860. A key example is the conversion of pinacol to pinacolone using sulfuric acid. The reaction proceeds through protonation, dehydration, rearrangement, and dehydrogenation steps. The migratory aptitude is influenced by electronic effects and stability of the carbocation intermediate. The rearrangement has applications in synthesizing carbonyl compounds, cyclic ketones, spiro-compounds, and supports ring expansions and contractions.
The Suzuki reaction is an organic reaction where an organoboron compound reacts with an organohalide compound to form a carbon-carbon bond. It is catalyzed by palladium and involves three main steps - oxidative addition, transmetalation, and reductive elimination. The Suzuki reaction is widely used in chemical synthesis due to its mild reaction conditions, tolerance of functional groups, and ability to form C-C bonds under aqueous conditions.
Synthetic Reagent and Its Applications (M. Pharm)MohdShafeeque4
The document summarizes various synthetic reagents and their applications. It describes 12 reagents including aluminium isopropoxide, N-bromosuccinimide, diazomethane, dicyclohexylcarbodiimide, Wilkinson reagent, Wittig reagent, osmium tetroxide, titanium chloride, diazopropane, diethyl azodicarboxylate, triphenylphosphine, and BOP reagent. For each reagent, it provides information on chemical formula, structure, preparation method, and typical applications. The document serves as a useful reference for organic chemistry students and researchers.
IMPORTANT NAMED REACTIONS in Organic synthesis with Introduction, General Mechanism, and their synthetic application covering more than 20 named reactions in it.
The document summarizes the Suzuki and Shapiro reactions. The Suzuki reaction involves a palladium-catalyzed cross-coupling between organoboron compounds and organic halides to form carbon-carbon bonds. It proceeds through oxidative addition, transmetallation, and reductive elimination steps. The Shapiro reaction involves the base-catalyzed decomposition of tosyl hydrazones to form olefins. Both reactions have been used in the synthesis of various drugs and natural products.
The Mannich reaction involves the condensation of an enolizable carbonyl compound, an aldehyde such as formaldehyde, and an amine to form a β-amino carbonyl compound known as a Mannich base. The reaction proceeds via the initial addition of the amine to the aldehyde to form an iminium ion intermediate, which then reacts with the enol form of the carbonyl compound to eliminate a proton and form the Mannich base product. While versatile building blocks in organic synthesis, the Mannich reaction has limitations in terms of substrate scope and control of regio- and stereoselectivity. Examples of applications include the synthesis of tropinone, a precursor of atropine, as well
This document summarizes various types of rearrangement reactions in organic chemistry. It describes 15 categories of rearrangements including rearrangements to electron deficient carbons, nitrogens, and oxygens. For each category, 1-2 specific rearrangements are explained in more detail, including their mechanisms. Rearrangements discussed include the Wagner-Meerwein, Pinacol, Benzilic acid, Hofmann, Curtius, Lossen, Beckmann, Baeyer-Villiger, Stevens, Sommelet-Hauser, Wittig, Favorskii, Benzidine, Fries, and Claisen rearrangements. The document was prepared by a student as part of their coursework to provide an overview of
The Claisen rearrangement is a thermal rearrangement reaction discovered by Rainer Ludwig Claisen in which the allyl group of a phenolic allyl ether migrates ortho to the phenol group. Key characteristics of the Claisen rearrangement are the inversion of the migrating allyl carbon and the intramolecular, unimolecular nature of the reaction. The mechanism involves a cyclic transition state that allows for migration to the ortho position, or para if both ortho positions are blocked.
The Suzuki reaction is a palladium-catalyzed cross-coupling reaction between boronic acids or esters with organic halides, triflates, or other boron-containing compounds. This reaction occurs under basic conditions and leads to the formation of carbon-carbon single bonds, typically between an aryl or vinyl group and another aryl or vinyl group. It is commonly used to synthesize biaryl compounds. The reaction proceeds through oxidative addition, transmetallation, and reductive elimination steps. Key advantages are mild reaction conditions and availability of boronic acids. The Suzuki reaction has applications in synthesizing pharmaceuticals, agrochemicals, and natural products.
Prof. Corey introduced the chiral auxiliary (-)-8-phenylmenthol in 1978. He used it in his famous prostaglandin synthesis. Prof. Trost then introduced mandelic acid as a chiral auxiliary in 1980. In 1985, Prof. Whitesell introduced an alternative, (1R,2S)-trans-2-phenyl-1-cyclohexanol, since preparing menthol compounds is difficult. A chiral auxiliary is a temporary, optically active compound incorporated into a synthesis to control stereochemistry and selectively form one stereoisomer over the other. Important examples include Evans' oxazolidinones and their use in asymmetric alkylations.
The Ullmann reaction involves the condensation of aryl halides in the presence of finely divided copper or copper bronze at an elevated temperature to form diaryl derivatives. Two proposed mechanisms are the free radical mechanism, where copper generates an aryl radical, and the ionic mechanism, where an organocuprate intermediate is formed. The Ullmann reaction is useful for synthesizing biaryls, polyaryls, diaryl amines, diaryl ethers, and gossypol.
The document discusses the Diels-Alder reaction, which involves a diene reacting with a dienophile to form a six-membered ring. Key characteristics include versatility, stereoselectivity, and reversibility. The mechanism involves overlap of the HOMO of the diene and LUMO of the dienophile. The stereochemistry of products is governed by the cis principle and endo rule. Variations include retro Diels-Alder reactions and cycloadditions involving allyl cations/anions.
The Sonogashira cross-coupling reaction forms carbon-carbon bonds between a terminal alkyne and an aryl or vinyl halide using a palladium catalyst. It was developed in 1975 and offers milder conditions than previous coupling reactions, such as room temperature. The reaction employs both a palladium and copper catalyst, with the copper activating the alkyne. It has become a highly useful reaction for carbon-carbon bond formation and has applications in pharmaceuticals, natural products, and organic materials synthesis.
Elimination reactions involve the removal of atoms or groups of atoms from adjacent carbons of a molecule, forming multiple bonds. They are endothermic reactions that occur with heat. There are two main types: alpha elimination removes two ligands from the same atom, while beta elimination removes ligands from adjacent carbons. Elimination mechanisms include E1 (unimolecular), E2 (bimolecular), and E1cb (carbocation intermediate). E1 involves carbocation formation in two steps, E2 is a single-step process, and E1cb forms a carbanion intermediate. The type of mechanism depends on factors like the substrate structure and conditions used.
It includes the UGI reaction & Brook rearrangement.
mechanism & application also included that presentation.
student will be helpful for easilly available this reaction.
The document summarizes two organic reactions: the Dieckmann reaction and ozonolysis reaction. The Dieckmann reaction involves the intramolecular condensation of diesters in the presence of a strong base to form β-keto esters via a 5-exo-trig cyclization. It is used to synthesize cyclopentane and cyclohexane derivatives. Ozonolysis involves the cleavage of unsaturated bonds like alkenes and alkynes with ozone to form carbonyl groups. It can be used to oxidize alkenes into alcohols, aldehydes, ketones or carboxylic acids and is useful for structure elucidation of unknown compounds containing carbon-carbon double bonds.
The Wagner-Meerwein rearrangement is an organic reaction that converts an alcohol to an olefin using an acid catalyst. It involves the formation of a carbocation intermediate followed by a 1,2-shift of a group to form a more stable carbocation. This is then deprotonated to form the olefin product. It can be used to rearrange highly branched compounds and reduce ring strain in cyclic compounds. Examples include the rearrangement of neopentyl alcohols and bicyclic terpene derivatives.
The document discusses several heterocyclic compounds including quinolines, isoquinolines, and indoles. It summarizes key reactions used to synthesize these compounds, including the Combes, Friedlander, Knorr, and Skraup reactions for quinoline synthesis. It also discusses the Bischler-Napieralski, Pictet-Spengler, and Pomeranz-Fritsch reactions for isoquinoline synthesis and the Fischer, Madelung, and Reissert reactions for indole synthesis, along with mechanisms and examples of each reaction. Reactivity and substitution patterns are also covered for quinolines, isoquinolines and indoles.
This chapter discusses various addition reactions of alkenes, including electrophilic and free radical additions. Electrophilic additions follow Markovnikov's rule, adding the electrophile to the carbon with the greater number of hydrogens. Free radical additions proceed anti-Markovnikov. Other reactions covered include hydroboration-oxidation, oxymercuration-demercuration, halohydrin formation, epoxidation, and hydrogenation. Mechanisms are provided for each reaction type.
The Baeyer-Villiger oxidation reaction converts cyclic ketones to lactones and acyclic ketones to esters using a peroxy acid as the oxidizing agent. Adolf Baeyer and Victor Villiger first reported this reaction in 1899 using menthone and tetrahydrocarvone. The reaction involves the nucleophilic attack of the peroxy acid on the carbonyl carbon, followed by migration of an alkyl group to the oxygen and formation of the ester or lactone product. This reaction has been modified using hydrogen peroxide as the oxidant and various catalysts. It has applications in synthesizing pharmaceuticals, pheromones, and other fine chemicals.
Total synthesis of Sterpurenone New, Total Synthesis of (훽)-Cyperolone, Protecting Group-Free Total Synthesis of (−)-Lannotinidine B, Enantiospecific Total Synthesis of the (−)-Presilphiperfolan-8-ol, Enantioselective Total Synthesis of (−)-Pavidolide B, total synthesis of Eupalinilide E
The document describes a concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel multi-step strategy. Key steps include:
1) A three-component Passerini reaction between suitably protected alaninal, leucine isonitrile, and ornithine components to deliver adducts 10a,b in high yield.
2) Orthogonal N-deprotection of 10a led, via a smooth O- to N-acyl migration, to 11, which constitutes the entire skeleton of the eurystatins.
3) Subsequent deprotection, macrocyclization, elaboration, and final oxidation steps efficiently afforded
The document summarizes the pinacol-pinacolone rearrangement, which involves the conversion of a vicinal diol to a ketone or aldehyde in the presence of an acid. It was first described by German chemist William Rudolph Fittig in 1860. A key example is the conversion of pinacol to pinacolone using sulfuric acid. The reaction proceeds through protonation, dehydration, rearrangement, and dehydrogenation steps. The migratory aptitude is influenced by electronic effects and stability of the carbocation intermediate. The rearrangement has applications in synthesizing carbonyl compounds, cyclic ketones, spiro-compounds, and supports ring expansions and contractions.
The Suzuki reaction is an organic reaction where an organoboron compound reacts with an organohalide compound to form a carbon-carbon bond. It is catalyzed by palladium and involves three main steps - oxidative addition, transmetalation, and reductive elimination. The Suzuki reaction is widely used in chemical synthesis due to its mild reaction conditions, tolerance of functional groups, and ability to form C-C bonds under aqueous conditions.
Synthetic Reagent and Its Applications (M. Pharm)MohdShafeeque4
The document summarizes various synthetic reagents and their applications. It describes 12 reagents including aluminium isopropoxide, N-bromosuccinimide, diazomethane, dicyclohexylcarbodiimide, Wilkinson reagent, Wittig reagent, osmium tetroxide, titanium chloride, diazopropane, diethyl azodicarboxylate, triphenylphosphine, and BOP reagent. For each reagent, it provides information on chemical formula, structure, preparation method, and typical applications. The document serves as a useful reference for organic chemistry students and researchers.
IMPORTANT NAMED REACTIONS in Organic synthesis with Introduction, General Mechanism, and their synthetic application covering more than 20 named reactions in it.
The document summarizes the Suzuki and Shapiro reactions. The Suzuki reaction involves a palladium-catalyzed cross-coupling between organoboron compounds and organic halides to form carbon-carbon bonds. It proceeds through oxidative addition, transmetallation, and reductive elimination steps. The Shapiro reaction involves the base-catalyzed decomposition of tosyl hydrazones to form olefins. Both reactions have been used in the synthesis of various drugs and natural products.
The Mannich reaction involves the condensation of an enolizable carbonyl compound, an aldehyde such as formaldehyde, and an amine to form a β-amino carbonyl compound known as a Mannich base. The reaction proceeds via the initial addition of the amine to the aldehyde to form an iminium ion intermediate, which then reacts with the enol form of the carbonyl compound to eliminate a proton and form the Mannich base product. While versatile building blocks in organic synthesis, the Mannich reaction has limitations in terms of substrate scope and control of regio- and stereoselectivity. Examples of applications include the synthesis of tropinone, a precursor of atropine, as well
This document summarizes various types of rearrangement reactions in organic chemistry. It describes 15 categories of rearrangements including rearrangements to electron deficient carbons, nitrogens, and oxygens. For each category, 1-2 specific rearrangements are explained in more detail, including their mechanisms. Rearrangements discussed include the Wagner-Meerwein, Pinacol, Benzilic acid, Hofmann, Curtius, Lossen, Beckmann, Baeyer-Villiger, Stevens, Sommelet-Hauser, Wittig, Favorskii, Benzidine, Fries, and Claisen rearrangements. The document was prepared by a student as part of their coursework to provide an overview of
The Claisen rearrangement is a thermal rearrangement reaction discovered by Rainer Ludwig Claisen in which the allyl group of a phenolic allyl ether migrates ortho to the phenol group. Key characteristics of the Claisen rearrangement are the inversion of the migrating allyl carbon and the intramolecular, unimolecular nature of the reaction. The mechanism involves a cyclic transition state that allows for migration to the ortho position, or para if both ortho positions are blocked.
The Suzuki reaction is a palladium-catalyzed cross-coupling reaction between boronic acids or esters with organic halides, triflates, or other boron-containing compounds. This reaction occurs under basic conditions and leads to the formation of carbon-carbon single bonds, typically between an aryl or vinyl group and another aryl or vinyl group. It is commonly used to synthesize biaryl compounds. The reaction proceeds through oxidative addition, transmetallation, and reductive elimination steps. Key advantages are mild reaction conditions and availability of boronic acids. The Suzuki reaction has applications in synthesizing pharmaceuticals, agrochemicals, and natural products.
Prof. Corey introduced the chiral auxiliary (-)-8-phenylmenthol in 1978. He used it in his famous prostaglandin synthesis. Prof. Trost then introduced mandelic acid as a chiral auxiliary in 1980. In 1985, Prof. Whitesell introduced an alternative, (1R,2S)-trans-2-phenyl-1-cyclohexanol, since preparing menthol compounds is difficult. A chiral auxiliary is a temporary, optically active compound incorporated into a synthesis to control stereochemistry and selectively form one stereoisomer over the other. Important examples include Evans' oxazolidinones and their use in asymmetric alkylations.
The Ullmann reaction involves the condensation of aryl halides in the presence of finely divided copper or copper bronze at an elevated temperature to form diaryl derivatives. Two proposed mechanisms are the free radical mechanism, where copper generates an aryl radical, and the ionic mechanism, where an organocuprate intermediate is formed. The Ullmann reaction is useful for synthesizing biaryls, polyaryls, diaryl amines, diaryl ethers, and gossypol.
The document discusses the Diels-Alder reaction, which involves a diene reacting with a dienophile to form a six-membered ring. Key characteristics include versatility, stereoselectivity, and reversibility. The mechanism involves overlap of the HOMO of the diene and LUMO of the dienophile. The stereochemistry of products is governed by the cis principle and endo rule. Variations include retro Diels-Alder reactions and cycloadditions involving allyl cations/anions.
The Sonogashira cross-coupling reaction forms carbon-carbon bonds between a terminal alkyne and an aryl or vinyl halide using a palladium catalyst. It was developed in 1975 and offers milder conditions than previous coupling reactions, such as room temperature. The reaction employs both a palladium and copper catalyst, with the copper activating the alkyne. It has become a highly useful reaction for carbon-carbon bond formation and has applications in pharmaceuticals, natural products, and organic materials synthesis.
Elimination reactions involve the removal of atoms or groups of atoms from adjacent carbons of a molecule, forming multiple bonds. They are endothermic reactions that occur with heat. There are two main types: alpha elimination removes two ligands from the same atom, while beta elimination removes ligands from adjacent carbons. Elimination mechanisms include E1 (unimolecular), E2 (bimolecular), and E1cb (carbocation intermediate). E1 involves carbocation formation in two steps, E2 is a single-step process, and E1cb forms a carbanion intermediate. The type of mechanism depends on factors like the substrate structure and conditions used.
It includes the UGI reaction & Brook rearrangement.
mechanism & application also included that presentation.
student will be helpful for easilly available this reaction.
The document summarizes two organic reactions: the Dieckmann reaction and ozonolysis reaction. The Dieckmann reaction involves the intramolecular condensation of diesters in the presence of a strong base to form β-keto esters via a 5-exo-trig cyclization. It is used to synthesize cyclopentane and cyclohexane derivatives. Ozonolysis involves the cleavage of unsaturated bonds like alkenes and alkynes with ozone to form carbonyl groups. It can be used to oxidize alkenes into alcohols, aldehydes, ketones or carboxylic acids and is useful for structure elucidation of unknown compounds containing carbon-carbon double bonds.
The Wagner-Meerwein rearrangement is an organic reaction that converts an alcohol to an olefin using an acid catalyst. It involves the formation of a carbocation intermediate followed by a 1,2-shift of a group to form a more stable carbocation. This is then deprotonated to form the olefin product. It can be used to rearrange highly branched compounds and reduce ring strain in cyclic compounds. Examples include the rearrangement of neopentyl alcohols and bicyclic terpene derivatives.
The document discusses several heterocyclic compounds including quinolines, isoquinolines, and indoles. It summarizes key reactions used to synthesize these compounds, including the Combes, Friedlander, Knorr, and Skraup reactions for quinoline synthesis. It also discusses the Bischler-Napieralski, Pictet-Spengler, and Pomeranz-Fritsch reactions for isoquinoline synthesis and the Fischer, Madelung, and Reissert reactions for indole synthesis, along with mechanisms and examples of each reaction. Reactivity and substitution patterns are also covered for quinolines, isoquinolines and indoles.
This chapter discusses various addition reactions of alkenes, including electrophilic and free radical additions. Electrophilic additions follow Markovnikov's rule, adding the electrophile to the carbon with the greater number of hydrogens. Free radical additions proceed anti-Markovnikov. Other reactions covered include hydroboration-oxidation, oxymercuration-demercuration, halohydrin formation, epoxidation, and hydrogenation. Mechanisms are provided for each reaction type.
The Baeyer-Villiger oxidation reaction converts cyclic ketones to lactones and acyclic ketones to esters using a peroxy acid as the oxidizing agent. Adolf Baeyer and Victor Villiger first reported this reaction in 1899 using menthone and tetrahydrocarvone. The reaction involves the nucleophilic attack of the peroxy acid on the carbonyl carbon, followed by migration of an alkyl group to the oxygen and formation of the ester or lactone product. This reaction has been modified using hydrogen peroxide as the oxidant and various catalysts. It has applications in synthesizing pharmaceuticals, pheromones, and other fine chemicals.
Total synthesis of Sterpurenone New, Total Synthesis of (훽)-Cyperolone, Protecting Group-Free Total Synthesis of (−)-Lannotinidine B, Enantiospecific Total Synthesis of the (−)-Presilphiperfolan-8-ol, Enantioselective Total Synthesis of (−)-Pavidolide B, total synthesis of Eupalinilide E
The document describes a concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel multi-step strategy. Key steps include:
1) A three-component Passerini reaction between suitably protected alaninal, leucine isonitrile, and ornithine components to deliver adducts 10a,b in high yield.
2) Orthogonal N-deprotection of 10a led, via a smooth O- to N-acyl migration, to 11, which constitutes the entire skeleton of the eurystatins.
3) Subsequent deprotection, macrocyclization, elaboration, and final oxidation steps efficiently afforded
1) Torulaspora delbrueckii was used to biotransform 30g of benzaldehyde into 22.9g of L-phenylacetylcarbinol (L-PAC) in a 5L stirred tank reactor.
2) L-PAC was then converted to ephedrine in two microwave-assisted steps: first L-PAC was transformed to 2-(methylimino)-1-phenyl-1-propanol, then this was reduced to ephedrine.
3) The identities of the products were confirmed using 1H NMR and FT-IR analysis, demonstrating a facile synthesis of ephedrine from benzaldehyde using biocatalysis and microwave-assisted chemistry.
1) A solid-phase method for synthesizing oxazolidinones is described which uses solid-phase activation/cycloelimination (SP/ACE). This involves attaching a 1,2-diol to a polymer-bound sulfonyl chloride, reacting one alcohol with an isocyanate, then cycloelimination to form the oxazolidinone.
2) A variety of oxazolidinones were synthesized in good overall yields using this method by changing the R groups on the isocyanate and diol substrates. Enantiopure oxazolidinones were also prepared using a chiral diol derived from D-mannitol.
3) The azidomethyl groups
This document describes a study on the preparation of oligoglucosamine by oxidative degradation of chitosan with hydrogen peroxide under microwave irradiation. The authors investigated the effects of various reaction parameters using an orthogonal test. They found that chitosan can be effectively degraded to oligoglucosamine with an average molecular weight of 900-1000 under optimal conditions of 15% H2O2 concentration and 4 minutes of microwave irradiation. The yield of oligoglucosamine depends strongly on the reaction time and H2O2 concentration.
This is ppt presentation of Dr. P.T. Perumal on the topic of preparation and reactions various Vilsmeir reagent and their applications in Heterocyclic chemistry.
This is very useful presentation and will be useful as a good reference for work on Heterocyclic chemistry.
This document describes a four-component one-pot process for synthesizing densely functionalized tartaric acid derivatives. The process involves a Passerini reaction followed by an aldol addition and a transesterification. In the first modification, carboxylic acids, isocyanides, and excess ethyl glyoxalate react to incorporate two ethyl glyoxalate residues, producing post-Passerini products in up to 41% yield. In the second modification, the initial Passerini reaction is followed by the addition of more ethyl glyoxalate, producing a second type of post-Passerini products through aldol addition and transesterification in up to 98% yield. The
The document provides information about quinoline, isoquinoline, and indole. It discusses their structures, properties, synthesis methods, and reactions. Quinoline and isoquinoline are both heterocyclic aromatic compounds composed of a benzene ring fused to a pyridine ring. They undergo similar electrophilic and nucleophilic substitution reactions. Common synthesis routes for quinoline include the Skraup, Doebner-Miller, and Conrad-Limpach reactions. Isoquinoline synthesis methods include the Pomeranz-Fritsch and Bischler-Napieralski reactions. Indole is a bicyclic molecule with a benzene and pyrrole ring. It does not readily
The document summarizes the career and research of Prof. Paul A. Grieco, including his education background, awards received, positions held, number of students mentored, and research interests. It provides an overview of his work developing reactions in highly polar media and applying these new methods to the total synthesis of various natural products. Examples discussed include the total syntheses of pseudotabersonine, ibogamine, eburnamonine, lycopodine, and fragments of epothilone B.
This document describes an efficient synthetic route to produce ethyl 2-aryl-4-hydroxy-1,3(2H,4H)-dioxoisoquinoline-4-carboxylates, which are known to inhibit auxin transport in plants and have plant growth regulating properties. The synthesis involves condensing anilines with homophthalic anhydride to form intermediates, which are then modified through various steps including acylation, enolate formation, alcoholysis, and oxygenation to produce the target compounds. Several of the target compounds showed potent auxin transport inhibition and plant growth regulating activity in tests.
This document discusses the Shapiro reaction, which was discovered by Robert H. Shapiro in 1967. The reaction involves converting aryl sulfonyl hydrazones of aldehydes and ketones into olefins using alkyl lithium reagents, grignard reagents, or alkali metal amides at -78°C. The reaction mechanism proceeds through deprotonation, elimination, and loss of nitrogen to form alkenyl intermediates. The Shapiro reaction has been used in the total synthesis of natural products like phytocassane D and in the formation of ring B in the Nicolaou Taxol total synthesis.
Condensation reactions involve the combination of two molecules with the loss of a small molecule like water. Aldol condensation forms carbon-carbon bonds by reacting an enolate ion with a carbonyl compound. It plays a role in gluconeogenesis, photosynthesis, and producing perfumes. Other condensation reactions discussed include Claisen, Knoevenagel, Schiff base formation, and Dieckmann cyclization. Condensation polymers are formed through condensation reactions and examples include nylon and DNA. Condensation reactions are widely used in organic synthesis and producing pharmaceuticals, fragrances, and polymers.
This document discusses metathesis reactions and their applications in organic synthesis. It begins with definitions and examples of different types of metathesis reactions including alkene, alkyne, and enyne metathesis. It then covers the key catalysts used, such as Grubbs and Schrock catalysts, as well as the 2005 Nobel Prize awarded for the development of metathesis reactions. The document concludes by outlining several important applications of metathesis in synthesizing biologically active compounds and natural products.
APPLICATIONS OF MULTICOMPONENT ASSEMBLY PROCESSES TO THE FACILE SYNTHESES OF ...JamesSahn
Several multicomponent assembly processes have been developed for the synthesis of intermediates that may be elaborated by a variety of cyclizations to generate a diverse array of highly functionalized heterocycles from readily-available starting materials. The overall approach enables the efficient preparation of libraries of small molecules derived from fused, privileged scaffolds. Source: Heterocycles 84:2 2012 pg 1089-1112
The Chichibabin reaction is a method for producing 2-aminopyridine derivatives by the reaction of pyridine with sodium amide. It was reported by Aleksei Chichibabin in 1914. The following is the overall form of the general reaction: The direct amination of pyridine with sodium amide takes place in liquid ammonia
The document summarizes 5 research studies conducted by B. V. Subba Reddy and colleagues on the synthesis of various heterocyclic compounds using transition metal catalyzed reactions of diazoketones and related substrates:
1. Synthesis of 2,3-disubstituted indoles and 2,4,5-trisubstituted pyrroles from α-diazoketones using Cu(OTf)2 catalysis. Application to the synthesis of the natural product Homofascaplysin C.
2. Acetal-initiated Prins bicyclization for the synthesis of furo[3,4-c]furan lignans and pyrano[3
This document describes a biomimetic approach to synthesizing the tricyclic core structure of xyloketals. The key steps involve an ortho ester Claisen rearrangement of a chromenol to form a rearranged ester, followed by an intramolecular cationic cyclization to form the tricyclic ketal ring system. This strategy was applied to synthesize alboatrin in high yields through a short and stereocontrolled route. During the synthesis, an unexpected epi-to-natural isomerization was observed, further improving the overall yield.
The document summarizes various applications of the Mukaiyama aldol reaction. It describes how esters can be used in place of aldehydes in the reaction. It also discusses the use of the reaction in the synthesis of functionalized diazoacetoacetates, the enantioselective catalytic version of the reaction in aqueous media, and its application in the vinylogous form to synthesize natural products like Khafrefungin. Finally, it mentions the asymmetric synthesis of anti-β-hydroxy-α-amino acid derivatives and a new approach to steroid skeleton synthesis using Mukaiyama reactions.
The document discusses indole, an aromatic heterocyclic compound consisting of a benzene ring fused to a pyrrole ring. It notes that indole and its substituted derivatives have diverse biological activities and are found in natural products and pharmaceuticals. Some key points made in the document include:
- Indole derivatives are used in many drug classes including antihypertensives, antidepressants, antipsychotics, NSAIDs, and more.
- Several total syntheses of complex indole natural products are described, utilizing reactions like intermolecular indole aryne cycloaddition.
- Methods for synthesizing substituted indoles are reviewed, such as the Fischer indole synthesis, Zn(OTf)2
Principles of Ion -exchange chromatography, High performance liquid chromatography (HPLC) , chromatography generally stands for a technique which separates mixtures based on different dynamic sharing of their components between two distinct physio-chemical environments called mobile and stationary phase by repeated absorption/desorption steps. Ion chromatography (IC) is a member of large family of liquid phase
chromatographic methods (that is a mobile phase is a liquid and a stationary phase is a
solid).
The document is a report on a seminar about ion exchange chromatography. It discusses the principles and mechanisms of ion exchange chromatography. Key points include:
- Ion exchange chromatography separates molecules based on differences in their net surface charge using anion or cation exchange resins with oppositely charged groups.
- Separation occurs as sample molecules reversibly adsorb to the ion exchanger via electrostatic interactions that can be controlled by modifying the pH or ionic strength of the mobile phase buffer.
- Different techniques like isocratic or gradient elution allow selective desorption and elution of sample components from the column.
- Proper choice of ion exchanger, buffer pH, and other parameters depends
acid base indicators, carbon acid, pH scale., carbanions, acids and conjugate bases, reactions of carbon acids, phosphonium ions as carbon acids , Carbon acids in synthesis, Super acid,
Maillard reaction is important for aroma, taste, and color in foods like roasted coffee beans, baked bread, and cooked meats. It involves a condensation reaction between reducing sugars and amino acids to form glycosylamine compounds, which then undergo rearrangement and further reactions depending on pH. In acidic conditions, these reactions form compounds like furfurals responsible for roasted flavors, while in basic conditions they form reductones and other products that contribute to toasted and caramelized aromas through additional reactions with amino acids.
Gluten is a protein found in wheat and related grains that provides texture to bread. It is made up of glutenin and gliadin proteins. When water is added to wheat flour during dough preparation, the glutenin and gliadin proteins come together through hydrogen bonding and disulfide bonds to form a elastic network that traps gas bubbles from yeast, allowing bread to rise during baking. Kneading the dough strengthens the gluten network. Less water makes for denser bread, while more water allows for lighter, higher rising bread through more efficient gas trapping by the gluten.
Garinor Ruano Stereoselective Synthesis in 2013, Bischler Napieralski cyclisation accelerated by microwave irradiation, . Racemic crispine A from 6,7-dimethoxy-1,2,3,4 tetrahydroisoquinoline
Food as a heterogeneous mixture, types of cooking, types of oils, chemistry of rancidity, uses of cooking , starch gelatinization in cooking rice, Maillard reaction, caramelisation
Carbenes- octet defying molecules, its fate, reactions, synthesis of carbenoids,spin multiplicity of carbenes triplet, singlet carbenes, Fischer and Schrock carbenes
Protecting group (PG) is a small molecule, to mask temporarily the a specific functional group of a molecule from undergoing reaction, allowing the rest of the functional groups present in the molecule to react without affecting the original reactivity and leave from the host molecule without affecting the rest of the functional groups.
The addition of protecting groups to functional groups is termed ‘protection’ and removal of protecting group is ‘deprotection’.
this presentation describes ways to enantiomeric product synthesis, hence introducing to chiral catalysts. the temperature effects are discussed with relation to soai autocatalysis. it shows introduction to stereocartography.
this presentation describes ways to enantiomeric product synthesis, hence introducing to chiral catalysts. the temperature effects are discussed with relation to soai autocatalysis. it shows introduction to stereocartography.
This is a document presentation of identification of major classes of organic compounds using IR spectroscopy. This is based on the book Wiley: Spectrometric Identification of Organic Compounds, by Robert Silverstein, 8th Edition .
The document discusses designing artificial photosynthetic systems inspired by natural photosynthesis. It summarizes the key processes in natural photosynthesis including light absorption, charge separation, and using the energy to fix carbon and reduce NADP+. It also discusses challenges in designing artificial solar energy storage systems, including controlling light harvesting and charge separation/transport while avoiding recombination. Perfect light harvesting systems are outlined as having high absorption, long-lived excited states, and catalytic properties while maintaining stability.
ESR spectroscopy in liquid food and beverages.pptxPRIYANKA PATEL
With increasing population, people need to rely on packaged food stuffs. Packaging of food materials requires the preservation of food. There are various methods for the treatment of food to preserve them and irradiation treatment of food is one of them. It is the most common and the most harmless method for the food preservation as it does not alter the necessary micronutrients of food materials. Although irradiated food doesn’t cause any harm to the human health but still the quality assessment of food is required to provide consumers with necessary information about the food. ESR spectroscopy is the most sophisticated way to investigate the quality of the food and the free radicals induced during the processing of the food. ESR spin trapping technique is useful for the detection of highly unstable radicals in the food. The antioxidant capability of liquid food and beverages in mainly performed by spin trapping technique.
Unlocking the mysteries of reproduction: Exploring fecundity and gonadosomati...AbdullaAlAsif1
The pygmy halfbeak Dermogenys colletei, is known for its viviparous nature, this presents an intriguing case of relatively low fecundity, raising questions about potential compensatory reproductive strategies employed by this species. Our study delves into the examination of fecundity and the Gonadosomatic Index (GSI) in the Pygmy Halfbeak, D. colletei (Meisner, 2001), an intriguing viviparous fish indigenous to Sarawak, Borneo. We hypothesize that the Pygmy halfbeak, D. colletei, may exhibit unique reproductive adaptations to offset its low fecundity, thus enhancing its survival and fitness. To address this, we conducted a comprehensive study utilizing 28 mature female specimens of D. colletei, carefully measuring fecundity and GSI to shed light on the reproductive adaptations of this species. Our findings reveal that D. colletei indeed exhibits low fecundity, with a mean of 16.76 ± 2.01, and a mean GSI of 12.83 ± 1.27, providing crucial insights into the reproductive mechanisms at play in this species. These results underscore the existence of unique reproductive strategies in D. colletei, enabling its adaptation and persistence in Borneo's diverse aquatic ecosystems, and call for further ecological research to elucidate these mechanisms. This study lends to a better understanding of viviparous fish in Borneo and contributes to the broader field of aquatic ecology, enhancing our knowledge of species adaptations to unique ecological challenges.
The technology uses reclaimed CO₂ as the dyeing medium in a closed loop process. When pressurized, CO₂ becomes supercritical (SC-CO₂). In this state CO₂ has a very high solvent power, allowing the dye to dissolve easily.
Describing and Interpreting an Immersive Learning Case with the Immersion Cub...Leonel Morgado
Current descriptions of immersive learning cases are often difficult or impossible to compare. This is due to a myriad of different options on what details to include, which aspects are relevant, and on the descriptive approaches employed. Also, these aspects often combine very specific details with more general guidelines or indicate intents and rationales without clarifying their implementation. In this paper we provide a method to describe immersive learning cases that is structured to enable comparisons, yet flexible enough to allow researchers and practitioners to decide which aspects to include. This method leverages a taxonomy that classifies educational aspects at three levels (uses, practices, and strategies) and then utilizes two frameworks, the Immersive Learning Brain and the Immersion Cube, to enable a structured description and interpretation of immersive learning cases. The method is then demonstrated on a published immersive learning case on training for wind turbine maintenance using virtual reality. Applying the method results in a structured artifact, the Immersive Learning Case Sheet, that tags the case with its proximal uses, practices, and strategies, and refines the free text case description to ensure that matching details are included. This contribution is thus a case description method in support of future comparative research of immersive learning cases. We then discuss how the resulting description and interpretation can be leveraged to change immersion learning cases, by enriching them (considering low-effort changes or additions) or innovating (exploring more challenging avenues of transformation). The method holds significant promise to support better-grounded research in immersive learning.
The binding of cosmological structures by massless topological defectsSérgio Sacani
Assuming spherical symmetry and weak field, it is shown that if one solves the Poisson equation or the Einstein field
equations sourced by a topological defect, i.e. a singularity of a very specific form, the result is a localized gravitational
field capable of driving flat rotation (i.e. Keplerian circular orbits at a constant speed for all radii) of test masses on a thin
spherical shell without any underlying mass. Moreover, a large-scale structure which exploits this solution by assembling
concentrically a number of such topological defects can establish a flat stellar or galactic rotation curve, and can also deflect
light in the same manner as an equipotential (isothermal) sphere. Thus, the need for dark matter or modified gravity theory is
mitigated, at least in part.
Phenomics assisted breeding in crop improvementIshaGoswami9
As the population is increasing and will reach about 9 billion upto 2050. Also due to climate change, it is difficult to meet the food requirement of such a large population. Facing the challenges presented by resource shortages, climate
change, and increasing global population, crop yield and quality need to be improved in a sustainable way over the coming decades. Genetic improvement by breeding is the best way to increase crop productivity. With the rapid progression of functional
genomics, an increasing number of crop genomes have been sequenced and dozens of genes influencing key agronomic traits have been identified. However, current genome sequence information has not been adequately exploited for understanding
the complex characteristics of multiple gene, owing to a lack of crop phenotypic data. Efficient, automatic, and accurate technologies and platforms that can capture phenotypic data that can
be linked to genomics information for crop improvement at all growth stages have become as important as genotyping. Thus,
high-throughput phenotyping has become the major bottleneck restricting crop breeding. Plant phenomics has been defined as the high-throughput, accurate acquisition and analysis of multi-dimensional phenotypes
during crop growing stages at the organism level, including the cell, tissue, organ, individual plant, plot, and field levels. With the rapid development of novel sensors, imaging technology,
and analysis methods, numerous infrastructure platforms have been developed for phenotyping.
When I was asked to give a companion lecture in support of ‘The Philosophy of Science’ (https://shorturl.at/4pUXz) I decided not to walk through the detail of the many methodologies in order of use. Instead, I chose to employ a long standing, and ongoing, scientific development as an exemplar. And so, I chose the ever evolving story of Thermodynamics as a scientific investigation at its best.
Conducted over a period of >200 years, Thermodynamics R&D, and application, benefitted from the highest levels of professionalism, collaboration, and technical thoroughness. New layers of application, methodology, and practice were made possible by the progressive advance of technology. In turn, this has seen measurement and modelling accuracy continually improved at a micro and macro level.
Perhaps most importantly, Thermodynamics rapidly became a primary tool in the advance of applied science/engineering/technology, spanning micro-tech, to aerospace and cosmology. I can think of no better a story to illustrate the breadth of scientific methodologies and applications at their best.
Authoring a personal GPT for your research and practice: How we created the Q...Leonel Morgado
Thematic analysis in qualitative research is a time-consuming and systematic task, typically done using teams. Team members must ground their activities on common understandings of the major concepts underlying the thematic analysis, and define criteria for its development. However, conceptual misunderstandings, equivocations, and lack of adherence to criteria are challenges to the quality and speed of this process. Given the distributed and uncertain nature of this process, we wondered if the tasks in thematic analysis could be supported by readily available artificial intelligence chatbots. Our early efforts point to potential benefits: not just saving time in the coding process but better adherence to criteria and grounding, by increasing triangulation between humans and artificial intelligence. This tutorial will provide a description and demonstration of the process we followed, as two academic researchers, to develop a custom ChatGPT to assist with qualitative coding in the thematic data analysis process of immersive learning accounts in a survey of the academic literature: QUAL-E Immersive Learning Thematic Analysis Helper. In the hands-on time, participants will try out QUAL-E and develop their ideas for their own qualitative coding ChatGPT. Participants that have the paid ChatGPT Plus subscription can create a draft of their assistants. The organizers will provide course materials and slide deck that participants will be able to utilize to continue development of their custom GPT. The paid subscription to ChatGPT Plus is not required to participate in this workshop, just for trying out personal GPTs during it.
1. Assignment
In
Hundred named Reactions used in Organic Syntheses
Submitted by
Roshen Reji Idiculla
ID MS14/11
Submitted to
Prof. Dr. Ibnu Saud
SI.
NO
NAME REACTION REAGENTS
CONDITIONS
Yi
eld
1. Robinson annulation Et3N
0 °C to RT, 7 h
EWG activated
π systems
78 Total Synthesis of (-)-Chromodorolide B J. Am. Chem. Soc., 2016, 138 (7), pp 2186–2189
substrate product
Michael addition (attack of
stabilized carbon nucleophiles on
EWG activated π systems) of
prochiral 3 with enone 4 (α,
unsaturated ketone). The generation
of C nucleophiles (Michael donor)
require use of non-nucleophilic
bases.
Then Intramolecular aldol reaction
Base catalyzed dehydration yielding
substituted cyclohexenone
2 Cu-Al Ox-mediated enone allylic
hydroxylation
Cu-Al
ether
85 This was used in total synthesis of Pavidolide B
substrate product
2. 3
.
Mitsunobu reaction 90
substrate product
Converts an alcohol into a variety of
functional groups.
an inversion of stereochemistry
4 meyer-schuster-rearrangement 82 Total synthesis of (-)-enigmazole A. doi 10.1002/anie.201801561 , gold-catalyzed Meyer–Schuster-
type rearrangement of propargylic benzoate.substrate product
secondary and
tertiary
propargyl
alcohols
α,β-unsaturated
ketones
acid-catalyzed rearrangement of
secondary and tertiary propargyl
alcohols to α,β-unsaturated ketones
5. Evans–Tishchenko reaction 90 This is used in Total synthesis of (-)-enigmazole A. doi 10.1002/anie.201801561
substrate product
β-hydroxy
ketones
1,3-anti diol
monoesters
diastereoselective reduction of β-
hydroxy ketones to the
corresponding 1,3-anti diol
monoesters
Lewis acid samarium iodide,
chelates aldehyde and ketone
oxygen in a Zimmweman taxler
model, 6-membered transition state.
The aldehyde formyl hydrogen
migrate intramolecularly to anti
diastereoselectivity
6 krapcho-decarboxylation 78 This is used in total synthesis of (+) Aplykurodinone-1 Org. Lett. 2017, 19, 18, 4861-4863
substrate product
3. ester having an
electron-
withdrawing
group in the beta
position
alkane
involves loss of an alkoxycarbonyl
group from ester having an electron-
withdrawing group in the beta
position
7 Lemieux-Johnson oxidation 84 This is used in total synthesis of Magellanine, McGee, P.; Bétournay, G.; Barabé, F.; Barriault,* L.
Angew. Chem. Int. Ed. 2017, 56, 6280-6283substrate product
Olefin two aldehyde or
ketone units
involves oxidative cleavage of a
olefin to form two aldehyde or
ketone units. 1st
step is
dihydroxylation of the alkene by
osmium tetroxide, followed by a
Malaprade reaction to cleave the
diol using periodate
8 Corey–Fuchs alkynylation 78 This is used in Total synthesis of (-)-enigmazole A. doi 10.1002/anie.201801561
substrate product
invovles formation of the 1,1-
dibromoolefins from aldehydes via
phosphine-dibromomethylenes,
which is then converted to to
alkynes , by Buttenberg–Wiechell
rearrangement
9 peterson-olefination This is used in total synthesis of Tetrodotoxin, Maehara, T,; Motoyama, K.; Toma, T.; Yokoshima, S.;
Fukuyama, T Angew. Chem. Int. Ed. 2017, 56, 1549-1552substrate product
α-silyl with
ketones (or
aldehydes)
a β-hydroxysilane
involves formation of a β-
hydroxysilane from α-silyl with
ketones (or aldehydes) which then
eliminates to form alkenes.
10
yamaguchi-esterification 85 This is used in total synthesis of Tetrodotoxin, Maehara, T,; Motoyama, K.; Toma, T.; Yokoshima, S.;
Fukuyama, T Angew. Chem. Int. Ed. 2017, 56, 1549-1552substrate product
aliphatic
carboxylic
acid
mixed anhydride
4. involves formation of mixed
anhydride from aliphatic carboxylic
acid and 2,4,6-trichlorobenzoyl
chloride (TCBC, Yamaguchi
reagent) . this mixed anhydride
which, react with an alcohol in the
presence of stoichiometric amount
of DMAP, giving desired ester.
11 finkelstein-reaction 74 This is used in Total synthesis of Sterpurenone, , Sahu, R.; Singh, V. J. Org. Chem. 2017, 82, 6268-
6278substrate product
involves SN2 reaction (Substitution
Nucleophilic Bimolecular reaction)
that involves the exchange of one
halogen atom as nucleophile.
12 pauson-khand-reaction 90 this is used in Total synthesis of Ryanodol, Chuang, K. V.; Xu, C.; Reisman, S. E. Science 2016, 353,
912.substrate product
involves [2+2+1] cycloaddition
between an alkyne, an alkene and
carbon monoxide to form a α,β-
cyclopentenone.
13 Michaelis–Arbuzov reaction 94 This is used in total synthesis of Rubriflordilactone B, Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A. Angew.
Chem. Int. Ed. 2016, 55, 6964.substrate product
(also called the Arbuzov reaction)
involves pentavalent phosphorus
species like phosphonates from
trivalent phosphorus ester with an
alkyl halide
14 Dieckmann condensation
NaBH4
91 This is used in total synthesis of Rubriflordilactone B, Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A. Angew.
Chem. Int. Ed. 2016, 55, 6964.substrate product
involves intramolecular reaction of
diesters with base to give β-keto
esters
15 fischer-indole-synthesis 75 This is used in Synthesis of Spiroindimicin B. Chem. Commun. 2016, 52, 800.
Substrate product
5. involves formation of a indole from
a (substituted) phenylhydrazine and
an aldehyde or ketone under acidic
conditions
16 wohl-ziegler-reaction 95
This is used in Synthesis of Spiroindimicin B. Chem. Commun. 2016, 52, 800.substrate product
involves formation of allylic or
benzylic bromides using an N-
bromosuccinimide and a radical
initiator Then Intramolecular aldol
reaction
Base catalyzed dehydration yielding
substituted cyclohexenone
17 Barton–Zard_reaction 88
This is used in Synthesis of Spiroindimicin B. Chem. Commun. 2016, 52, 800.substrate product
involves formation of pyrrole
derivatives via the reaction of a
nitroalkene with an α-
isocyanoacetate under basic
conditions.
18 gassman-indole-synthesis 77 This is used in total synthesis of Leuconoxine Chem. Eur. J. 2015, 21, 6355.
substrate product
6. involves formation of substituted
indoles by addition of an aniline and
a ketone bearing a thioether
substituent
19 parikh-doering-oxidation 89
This is used in total synthesis of Leuconoxine, Chem. Eur. J. 2015, 21, 6355.substrate product
oxidation involves oxidation of
primary and secondary alcohols into
aldehydes and ketones. Using
dimethyl sulfoxide (DMSO) as the
oxidant, activated by the sulfur
trioxide pyridine complex in the
presence of triethylamine base.
20 Darzens reaction 96
This is used in Total synthesis of Rubrobramide, Mizutani, S.; Komori, K.; Taniguchi, T.; Monde, K.;
Kuramochi, K.; Tsubaki, K. Angew. Chem. Int. Ed. 2016, 55, 9553-9556.
substrate product
(also known as the Darzens
condensation or glycidic ester
condensation) involves formation of
α,β-epoxy ester from ketone or
aldehyde with an α-haloester in the
presence of a base.
21 rubottom-oxidation 76 This is used in Synthesis of Kinamycin F. J. Am. Chem. Soc. 2010, 132, 2540.
substrate product
involves formation of α-hydroxy
carbonyl product from silyl enol
ethers and peroxyacids
22 ley-griffith-oxidation 91 This is used in Synthesis of Caribenol A, J. Am. Chem. Soc. 2010, 132, 13608.
substrate product
7. Involves selective oxidation of
alcohols to aldehydes or ketones
23 pinnick-lindgren-oxidation 89 this is used in Total synthesis of Vincorine, Horning, B. D.; MacMillan, D. W. C. J. Am.Chem. Soc.
2013, 135, 6442-6445.substrate Product
involves oxidation of aldehydes into
carboxylic acids using sodium
chlorite (NaClO2) under mild acidic
conditions
24 shapiro-reaction 85 This is used in Total synthesis of Artemisinin, Zhu, C.; Cook, S. P. J. Am. Chem. Soc. 2012, 134,
13577-13579substrate product
involves conversion of ketone or
aldehyde to an alkene through an
intermediate hydrazone in the
presence of 2 equivalents of
organolithium reagent
25 julia-kociensky-olefination 83 This is used in Total synthesis of Apiosporic Acid, Gärtner, M.; Kossler, D.; Pflästerer, D.; Helmchen,
G. J. Org. Chem, 2012, 77, 4491-4495substrate product
involves reaction of phenyl sulfones
with aldehydes (or ketones) to give
E alkenes
26 . saegusa-ito-oxidation 95 This is used in Total synthesis of Cycloclavine, Petronijevic, F. R.; Wipf, P. J. Am. Chem. Soc. 2011,
133, 7704–77079substrate product
8. involves formation of α-β
unsaturated carbonyl compounds,
from silyl enol ether and
palladium(II) acetate
27 lemieux-johnson-oxidation 89 This is used in Synthesis of Solandelactone E, Angew. Chem. Int. Ed. 2010, 49, 6673
substrate product
involves oxidative cleavage of
olefins to aldehydes or ketones
28 rosenmund-von-braun-reaction 80 this is used in Synthesis of Ammosamide B J. Am. Chem. Soc. 2010, 132, 2528.
substrate product
involves formation of an aryl nitrile
from aryl halide and cuprous
cyanide
29 fischer-esterification 86 this is used in Synthesis of Ammosamide B J. Am. Chem. Soc. 2010, 132, 2528.
substrate product
involves ester formation from
primary, secondary alcohols ,
phenols in acidic medium
30 overman-rearrangement benzene 97 This is used in Synthesis of Aspidofractinine, J. Org. Chem. 2009, 74, 6035.
substrate product
involves Claisen rearrangement of
allylic alcohols to give allylic
trichloroacetamides through an
imidate intermediate
9. 31 curtius-rearrangement 87
This is used in Synthesis of Oseltamivir Angew. Chem. Int. Ed. 2009, 48, 1304.
substrate product
involves thermal decomposition of
an acyl azide to an isocyanate with
loss of nitrogen gas.
32 williamson-ether-synthesis 95 This is used in Synthesis of Glycyrol, Tetrahedron Lett. 2008, 49, 6835.
substrate product
33 henry-reaction 96 This is used in Total synthesis of Nakadomarin A, Jakubec, P.; Cockfield, D. M.; Dixon, D. J. Am.
Chem. Soc. 2009, 131, 16632–16633substrate product
involves formation of β-Nitro
alcohols from nitroalkane and an
aldehyde or ketone in the presence
of a base
34 johnson-claisen-rearrangement 91 This is used in Synthesis of Nupharamine , Synlett 2010, 866.
substrate product
10. involves formation of γ,δ-
unsaturated ester, from allylic
alcohol and orthoester.
35 horner-wadsworth-emmons-reaction 78 This is used in Synthesis of Nupharamine , Synlett 2010, 866.
substrate product
involves formation of E-alkenes
from stabilized phosphonate
carbanions and aldehydes (or
ketones).
36 ramberg-baumlcklund-reaction 84 This is used in Synthesis of Aigialomycin D, J. Org. Chem. 2009, 74, 2271.
substrate product
involves formation of Z alkenes (
weak bases) , or E alkenes (strong
bases) from α-halosulfones
37 marko-lam-deoxygenation 25 This is used in Synthesis of Trifarienol B, Angew. Chem. Int. Ed. 2008, 47, 131.
substrate product
involves conversion of hydroxy
functional group in an organic
compound to a hydrogen atom to
give an alkyl group
38 morita-baylis-hillman-reaction 67 This is used in Synthesis of Grandisine D, Org. Lett. 2009, 11, 1179.
substrate product
11. involves C-C bond formation
between α-position of an activated
alkene and a carbon electrophile
such as an aldehyde using
nucleophilic catalyst, such as a
tertiary amine and phosphine.
39 barton-mccombie-reaction 94
This is used in Synthesis of Grandisine D, Org. Lett. 2009, 11, 1179.substrate product
40 evans-mislow-rearrangement 89 This is used in total Synthesis of Agelastatin A, Org. Lett. 2009, 11, 2687.
substrate product
involves formation of allylic
alcohols from allylic sulfoxides in a
2,3-sigmatropic rearrangement.
41 barton-vinyl-iodide-synthesis 65 this is used in Synthesis of Cortistatin A, J. Am. Chem. Soc. 2008, 130, 7241.
substrate product
involves formation of vinyl iodide
from a hydrazone iodine and a non-
nucleophilic base such as DBU
43 seyferth-gilbert-homologation 55 This is used in Synthesis of Alstonerine, J. Org. Chem. 2003, 68, 8867.
substrate product
involves formation of substituted
alkyne, from aryl ketone (or
aldehyde) with dimethyl
(diazomethyl)phosphonate and
potassium tert-butoxide. .
44 The_Schlosser modification 89 This is used I total Synthesis of Pseudolaric Acid B, J. Am. Chem. Soc. 2007, 129, 14556.
substrate product
12. involves formation of an alkene and
triphenylphosphine oxide from
aldehyde or ketone with an
unstabilised triphenyl phosphonium
ylide. The erythro betaine in Wittig
can be converted to the threo betaine
using phenyllithium at low
temperature, leading to E-alkene.
45 prilezhaev-reaction 98 This is used I total Synthesis of Pseudolaric Acid B, J. Am. Chem. Soc. 2007, 129, 14556.
substrate product
, involves formation of epoxides
from alkene and peroxy acid
46 benzoin-condensation 78 This is used in Synthesis of Kinamycin F, J. Am. Chem. Soc. 2007, 129, 10356.
substrate product
involves 1,2-addition reaction of two
aldehydes catalyzed by nucleophiles
such as a cyanide anion or an N-
heterocyclic carbene (usually
thiazolium salts ) forming an
aromatic acyloin
47 pinner-reaction 60 This is used in Synthesis of Oseltamivir, Org. Lett. 2007, 9, 259.
substrate product
involves formation of imino ester
salt, Pinners salt, from nitrile with an
alcohol.
13. 48 weinreb-ketone-synthesis 52 This is used in Synthesis of Nominine, J. Am. Chem. Soc. 2006, 128, 8734.
substrate product
, involves formation of ketones from
Weinreb–Nahm amide, and
organometallic reagent or carbon
nucleophiles
49 staudinger-reaction 56 This is used in Synthesis of Saxitoxin, J. Am. Chem. Soc. 2003, 125, 2028.
substrate product
involves formation of
triphenylphosphine phenylimide,
which on hydrolysis produces a
phosphine oxide and an amine
50 evans-saksena-reduction 90 This is used in Synthesis of Kinamycin C, J. Am. Chem. Soc. 2006, 128, 14790.
substrate product
involves diastereoselective reduction
of β-hydroxy ketones to the
corresponding anti-dialcohols,
employing the reagent
tetramethylammonium
triacetoxyborohydride
(Me4NHB(OAc)3).
51 kulinkovich reaction 60 This is used in Synthesis of B-Araneosene, J. Am. Chem. Soc. 2005, 127, 13813.
substrate product
involves formation of
cyclopropanols from reaction of
esters with dialkyldialkoxytitanium
reagents.
14. 52 fukuyama-indole-synthesis 52 This is used in Synthesis of Strychnine, J. Am. Chem. Soc. 2004, 126, 10246.
substrate product
involves formation of 2,3-
disubstituted indoles, from benzene
unit with o-isocyano carbon or 2-
alkenylthioanilide using tributyltin
hydride the reducing agent, and
azobisisobutyronitrile (AIBN) as a
radical initiator
53 larock-indole-synthesis 75 This is used in Synthesis of Strychnine, J. Am. Chem. Soc. 2004, 126, 10246.
substrate product
, involves formation of synthesize
indoles from an ortho-iodo aniline
and a disubstituted alkyne, using
heteroannulation reaction and
palladium as a catalyst
54 takai-reaction 79 This is used in Synthesis of Quinine, J. Am. Chem. Soc. 2004, 126, 706.
substrate Product
involves formation of alkene from
an aldehyde with a
diorganochromium compound
15. 55 grieco-dehydration 77 this is used in Synthesis of Quinine, Tetrahedron Lett. 2004, 45, 3783.
substrate Product
involves formation of a terminal
alkene by elimination reaction of an
aliphatic primary alcohol using
selenide
56 wolff-rearrangement 72 . This is used in Synthesis of Pentacycloanammoxic Acid, J. Am. Chem. Soc. 2004, 126, 15664.
substrate product
, involves formation of ketone from
α-diazocarbonyl compound by loss
of dinitrogen with accompanying
1,2-rearrangement
57 schmidt-reaction 86 This is used in Total synthesis of Stenine, Frankowski, K. J.; Golden, J. E.; Zeng, Y.; Lei, Y.; Aubé,
J. J. Am. Chem. Soc. 2008, 130, 6018–6024.substrate product
involves formation of amine
(carboxylic acid) or amide (ketone) ,
from reaction of azide reacts with a
carbonyl group
58 simmons-smith-reaction 75 This is used in Total synthesis of Hirsutene, Jiao, L.; Yuan, C.; Yu, Z.-X. J. Am. Chem. Soc. 2008,
130, 4421.
substrate product
involves formation of cyclopropane
from organozinc carbenoid and an
alkene.
59 nef-reaction 51 this is used in Total synthesis of Tetrodotoxin , Sato, K.; Akai, S.; Shoji, H.; Sugita, N.; Yoshida,
S.; Nagai, Y.; Suzuki, K.; Nakamura, Y.; Kajihara, Y.; Funabashi, M.; Yoshimura, J.; JOC. 2008,
73, 1234
substrate product
involves formation of ketone and
aldehyde from a primary or
secondary nitroalkane
60 liebeskind-srogl-coupling 94 This is used in Synthesis of Sphingosine. Org. Lett. 2007, 9, 2993.
16. substrate product
involves formation of carbon-carbon
bond from thioester and a boronic
acid using a metal catalyst
61 mukaiyama-aldol-addition 58 This is used in Total synthesis of Cryptocarya Diacetate. Boxer, M. B.; Yamamoto, H. J. Am. Chem.
Soc., 2007, 129, 2762-2763substrate product
involves aldol reaction between a
silyl enol ether and an aldehyde or
formate
62 maitland-japp-reaction 60 This is used in Synthesis of Centrolobine. Tetrahedron 2005, 61, 5433.
substrate product
involves two reactions. 1st
reaction
between the ketone and the aldehyde
catalyzed by base the bis Aldol
adduct is formed first. The second
step is a ring-closing reaction when
one hydroxyl group displaces the
other in a nucleophilic substitution
forming an oxo-tetrahydropyran.
63 baeyer-villiger-oxidation 61 . This is used in Synthesis of Reserpine, J. Am. Chem. Soc. 2005, 127, 16255.
substrate product
involves formation of an ester from
a ketone or a lactone from a cyclic
ketone, using peroxyacids or
peroxides as the oxidant
17. 64 fleming-tamao-oxidation 61 This is used in Synthesis of Reserpine, J. Am. Chem. Soc. 2005, 127, 16255.
substrate product
involves oxidation of carbon–silicon
bond to a carbon–oxygen bond with
a peroxy acid or hydrogen peroxide
65 neber-rearrangement 89 This is used in Synthesis of Dragmacidin F, J. Am. Chem. Soc. 2002, 124, 13179.
substrate product
, involves formation of alpha-
aminoketone from ketoxime via a
rearrangement reaction
66 stork danheiser reaction 59 This is used in Total synthesis of Platensimycin, Nicolaou, K. C.; Li, A.; Edmonds, D. J. Angew.
Chem. Int. Ed. 2006, 45, 7086.substrate product
involves reaction of the β alkoxy
ketene with an organometallic
compound followed by acid
treatment to obtain another ketene
reaction, and the position of the
carbonyl group of the newly formed
ketene is the olefinic carbon of the
enol ether in the starting material.
67 wacker-oxidation 95 This is used in Total synthesis of Dichroanone, McFadden, R. M.; Stoltz, B. M. J. Am. Chem. Soc.
2006, 128, 7738substrate product
involves oxidation of alkene to
ketone in the presence of
palladium(II) chloride as the
catalyst.
18. 68 fritsch-buttenberg-wiechell-
rearrangement
91 This is used in Total synthesis of Amphidinolide E, Va, P.; Roush, W. R. J. Am. Chem. Soc. 2006,
128, 15960.
substrate product
involves rearrangmente of 1,1-
diaryl-2,2-dibromo-alkene to alkyne
by reaction with a strong base
69 ullmann-coupling 85 This is used in Total synthesis of Staphacidin, Herzon, S. B.; Myers, A. G J. Am. Chem. Soc. 2005,
127, 5342substrate product
involves coupling reaction between
aryl halides and copper
70 grob-fragmentation
substrate product
involves elimination reaction of a
neutral aliphatic chain into three
fragments: a positive ion a
carbenium, carbonium or acylium
ion, an unsaturated neutral an
alkene, alkyne, or imine and a
negative ion (the "nucleofuge") tosyl
or hydroxyl ion:
71 corey-itsuno-reaction 75 This is used in Synthesis of Panaxytriol, J. Org. Chem. 2003, 68, 4519.
substrate product
also known as the Corey–Bakshi–
Shibata (CBS) reduction involves
formation of chiral, non-racemic
alcohol, from an achiral ketone
72 cadiot-chodkiewics-reaction 63 This is used in Synthesis of Panaxytriol, J. Org. Chem. 2003, 68, 4519.
substrate product
19. involves coupling reaction between
a terminal alkyne and a haloalkyne
catalyzed by a copper(I) salt such as
copper(I) bromide and an amine
base to form 1,3-diyne or di-alkyne.
73 lombardo-methylenation 72 This is used in Synthesis of Tetrodotoxin, J. Am. Chem. Soc. 2003, 125, 11510.
substrate product
involves methylation of unreactive
ketones
74 pechmann-condensation 47 This is used in Synthesis of Aflatoxin B1, J. Am. Chem. Soc. 2003, 125, 3090.
substrate product
synthesis of coumarins, starting
from a phenol and a carboxylic acid
or ester containing a β-carbonyl
group
75 corey-posner-whitesides-house-
reaction
95 this is used in Synthesis of Ingenol, J. Am. Chem. Soc. 2003, 125, 1498.
Substrate product
involves formation of a new alkane
from lithium diorganylcuprate
(R2CuLi) with an organyl
(pseudo)halide (R'X) .
76 Ritter reaction 73
this is used in enantiospecific synthesis of Jiadifenolide, http://dx.doi.org/10.1002/anie.201402335
substrate product
20. ,involves the acid-induced
nucleophilic addition of a nitrile to a
carbenium ion, followed by
hydrolysis to the corresponding
amide
77 blaise-reaction 67 This is used in Synthesis of (−)-Lasonolide A http//dx.doi.org/10.1021/ja411270d
substrate product
involves formation of β-ketoester
from the reaction of zinc metal with
a α-bromoester and a nitrile
78 marshall-propargylation 65 This is used in Synthesis of Amphidinolide F, http://dx.doi.org/10.1002/anie.201301700
substrate product
propargylation involves C-C
coupling between propargyl
mesylates and aldehydes .
79 Schwartz reaction 79
This is used in Synthesis of Branimycin, http://dx.doi.org/10.1002/chem.201200257
substrate product
, involves reaction of
organozirconium intermediates with
electrophiles iodine, bromine and
acid chlorides to give the
corresponding haloalkanes, and
ketones
80 Kornblum oxidation 76 this is used in synthesis of Deoxy-Penostatin A Snider, B. B.; Liu, T. J. Org. Chem. 2000, 65, 8490-
8498substrate product
involves reaction of a primary halide
with dimethyl sulfoxide (DMSO) to
form an aldehyde.
81 Arndt–Eistert reaction Ag(O2CCF3)2
Ag+ (cat)
88 This is used in synthesis of JuvabioneSoldermann, N.; Velker, J.; Vallet, O.; Stoeckli-Evans, H.;
Neier, R. Helv. Chim. Acta 2000, 83, 2266.substrate product
21. involves conversion of carboxylic
acid to a higher carboxylic acid
homologue
82 Jones oxidation 85 This is used in synthesis of Hispidospermidine, Frontier, A. J.; Raghavan, S.; Danishevsky, S. J. J.
Am. Chem. Soc. 2000, 122, 6151.substrate product
involves oxidation of primary and
secondary alcohols to carboxylic
acids and ketones, respectively
83 vilsmeier-haack-formylation 66 this is used in synthesis of Illudin C, Aungst, R. A.; Chan, C.; Funk, R. L. Org. Lett. 2001, 3, 2611.
substrate product
involves substituted amide with
phosphorus oxychloride and an
electron-rich arene or alkene to
produce an aryl aldehyde or ketone
84 pummerer-rearrangement 88 This is used in synthesis of Solanapyrone:, Hagiwara, H.; Kobayashi, K.; Miya, S.; Hoshi, T.;
Suzuki, T.; Ando, M.; Okamoto, T.; Kobayashi, M.; Yamamoto, I.; Ohtsubo, S.; Kato, M.; Uda, H.J.
Org. Chem. 2002, 67, 5969.
substrate product
involves rearrangement of alkyl
sulfoxide to an α-acyloxy–thioether
(monothioacetal-ester) in the
presence of acetic anhydride.
85 mcmurry-reaction 90 This is used in synthesis of (±)-δ-Araneosene, Hu, T.; Corey, E. J. Org. Lett. 2002, 4, 2441
substrate product
involves coupling of two ketone or
aldehyde groups to an alkene using a
titanium chloride compound such as
titanium(III) chloride and a reducing
agent
22. 86 Stobbe-condensation 98 This is used in synthesis of Acitretin, , Andriamialisoa, Z.; Valla, A.; Cartier, D.; Labia, R. Helv.
Chim. Acta 2002, 85, 2926.substrate product
modification of Claisen
condensation involving dialkyl ester
of carboxylic acid requiring less
strong bases
87 Reformatsky reaction
Zn
66 This is used in synthesis of Waol A, Gao, X.; Nakadai, M.; Snider, B. Org. Lett. 2003, 5, 451
substrate product
involves condensation of aldehydes
or ketones, with α-halo esters, using
a metallic zinc to form β-hydroxy-
esters
88 Corey winter reaction 76 This is used in synthesis of Astellatol. https://doi.org/10.1002/anie.201800167
substrate product
reaction involves Ei mechanism. It
converts vicinal diols to alkenes via
cyclic thionocarboxylates.
89 achmatowicz-reaction 90 This is used in Total Synthesis of Cyclocitrinol. J. Am. Chem. Soc., 2018, 140 (16), pp 5365–5369
substrate Product
involves rearrangement of furan to a
dihydropyran
91 Fukuyama reduction 97 This is used in Synthesis of Divergolide I, J. Am. Chem. Soc. 2018, 140, 8, 2748-2751
23. substrate Product
, involves reduction of a thioester is
to an aldehyde by a silyl hydride in
presence of a catalytic amount of
palladium
92 Shiina esterification 71 This is used in Synthesis of Divergolide I, J. Am. Chem. Soc. 2018, 140, 8, 2748-2751
substrate product
involves formation of carboxylic
esters from nearly equal amounts of
carboxylic acids and alcohols by
using aromatic carboxylic acid
anhydrides as dehydration
condensation agents.
92 Rautenstrauch reaction 80
This is used in Synthesis of (+)‐ and (±)‐Hosieine A, https://doi.org/10.1002/anie.201804076substrate product
involves gold-catalyzed cyclization
reactions using the activation of
alkynes by gold(I) to form
cyclopent-2-enones.
93 Dakin oxidation (or Dakin reaction) 58
This is used in Synthesis of (±)‐Phomoidride D https://doi.org/10.1002/anie.201712369substrate product
involves oxidation of ortho- or para-
hydroxylated phenyl aldehyde (2-
hydroxybenzaldehyde or 4-
hydroxybenzaldehyde) or ketone
with hydrogen peroxide in base to
form a benzenediol and a
carboxylate
94 Riley oxidation 47 This is used in Synthesis of Salimabromide,J. Am. Chem. Soc. 2018, 140, 27, 8444-8447
substrate product
24. involves selenium dioxide-mediated
oxidation of methylene groups
adjacent to carbonyls
95 hunsdiecker-reaction 87 This is used in synthesis of (±)-Aspergilline A, J. Am. Chem. Soc., 2017, 139 (51), pp 18504–18507
substrate product
involves reaction of silver salts of
carboxylic acids with halogen to
produce an organic halide.
96 Chugaev elimination 78
This is used in Synthesis of (±)-lycoricidine J. Org. Chem., 2007, 72, 2570-2582.
substrate product
an example of Ei mechanism ,
similar to ester pyrolysis. It
converts alcohols with 𝛽 H to
alkenes, via xanthate formation
97 friedlaender-synthesis.
BuLi
THF
Then MeOH
84 This is used in synthesis of poly-substituted quinolones, C.-S. Jia, Z. Zhang, S.-J. Tu, G.-W. Wang,
Org. Biomol. Chem., 2006, 4, 104-110.substrate product
Involves formation of quinoline
derivatives from 2-
aminobenzaldehydes with ketones
98 Pfitzner–Moffatt oxidation 78 This is used in Synthesis of 18R-hydroxy-epiallo-yohimbines https://doi.org/10.1016/S0040-
4039(00)00913-8
substrate product
25. 99 arbuzov-reaction. 75 This is used in Synthesis of (−)-Epibatidine ,Org. Lett., 2001, 3 (19), pp 3009–3012
substrate product
form a pentavalent phosphorus
species from a trivalent phosphorus
ester with an alkyl halide
100 (Fleming-) Tamao (-Kumada)
Oxidation
80 This is used in Total Synthesis of Eunicenone A
J. Am. Chem. Soc., 2001, 123 (9), pp 1872–1877substrate product
Oxidation of alkyl fluorosilanes to
the corresponding alcohols.