Retro synthesis
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The document discusses retrosynthesis, which is the process of working backward from a target organic compound to develop a synthetic route. It involves imagining the cleavage of bonds to form synthons, which are idealized fragments represented as ions. Key steps in retrosynthesis are disconnection, which breaks bonds, and functional group interconversion, which changes one functional group to another. The goal is to develop the most efficient synthesis using readily available starting materials and reagents.
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Retrosynthesis
This document discusses retrosynthetic analysis and disconnection strategies for planning the synthesis of drug molecules. It defines key terms like retrosynthesis, synthons, and functional group interconversions. It provides guidelines for disconnecting different types of bonds and functional groups in a molecule, including C-X, C-C, and multiple bonds/groups. The goal is to break down the target molecule into stable and readily available starting materials by applying principles of retrosynthetic analysis.
Retrosynthetic analysis in organic synthesis
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Retrosynthetic analysis is a technique used to plan organic syntheses by working backwards from the target molecule. It involves mentally deconstructing the target molecule through sequential disconnections and functional group transformations until commercially available starting materials are reached. Each disconnection produces synthons, which are idealized fragments that represent possible reaction precursors. Common types of disconnections include C-X, C-C, and carbonyl bonds. The goal of retrosynthesis is to simplify the target structure and design multiple possible synthesis routes leading from simple starting materials to the target. It helps chemists discover efficient syntheses by considering the reactivity, selectivity, and availability of materials at each step.
Ugi reaction
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.
Wiliknsons reagent
Wilkinson's catalyst, also known as chloridotris(triphenylphosphane)rhodium(I), is a coordination complex of rhodium with the formula RhCl(PPh3)3. It is a red-brown solid that is soluble in hydrocarbon solvents and used widely as a catalyst for hydrogenation of alkenes. Wilkinson's catalyst is obtained by treating rhodium(III) chloride hydrate with excess triphenylphosphine, which acts as a reducing agent to reduce rhodium from Rh(III) to Rh(I). It adopts a slightly distorted square planar structure and undergoes fast dynamic exchange processes in solution.
E1 &E2 mechanism, sandmeyer and benzyne mechanism
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.
synthon approach
1) The document discusses the synthon approach, which involves breaking down a target molecule into simpler starting materials through imaginary bond breaking (disconnection) or functional group interconversion.
2) Key terms are defined, including disconnection, synthon, and functional group interconversion. Basic rules of disconnection are outlined.
3) An example of using the synthon approach to synthesize the drug benzocaine from toluene is provided, outlining the multi-step reaction pathway and identifying specific synthons.
Michael addition reaction
The document discusses the Michael addition reaction, which involves the nucleophilic addition of a carbanion to an α,β-unsaturated carbonyl compound. It provides the definition, mechanism, examples including the synthesis of warfarin, and applications such as asymmetric Michael reactions. The mechanism involves deprotonation of the carbonyl compound by a base to form an enolate ion, which adds to the Michael acceptor to form a new carbon-carbon bond via 1,4-addition.
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This document discusses retrosynthetic analysis and disconnection strategies for planning the synthesis of drug molecules. It defines key terms like retrosynthesis, synthons, and functional group interconversions. It provides guidelines for disconnecting different types of bonds and functional groups in a molecule, including C-X, C-C, and multiple bonds/groups. The goal is to break down the target molecule into stable and readily available starting materials by applying principles of retrosynthetic analysis.
Retrosynthetic analysis in organic synthesis
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Retrosynthes analysis and disconnection approach
Retrosynthetic analysis is a technique used to plan organic syntheses by working backwards from the target molecule. It involves mentally deconstructing the target molecule through sequential disconnections and functional group transformations until commercially available starting materials are reached. Each disconnection produces synthons, which are idealized fragments that represent possible reaction precursors. Common types of disconnections include C-X, C-C, and carbonyl bonds. The goal of retrosynthesis is to simplify the target structure and design multiple possible synthesis routes leading from simple starting materials to the target. It helps chemists discover efficient syntheses by considering the reactivity, selectivity, and availability of materials at each step.
Ugi reaction
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.
Wiliknsons reagent
Wilkinson's catalyst, also known as chloridotris(triphenylphosphane)rhodium(I), is a coordination complex of rhodium with the formula RhCl(PPh3)3. It is a red-brown solid that is soluble in hydrocarbon solvents and used widely as a catalyst for hydrogenation of alkenes. Wilkinson's catalyst is obtained by treating rhodium(III) chloride hydrate with excess triphenylphosphine, which acts as a reducing agent to reduce rhodium from Rh(III) to Rh(I). It adopts a slightly distorted square planar structure and undergoes fast dynamic exchange processes in solution.
E1 &E2 mechanism, sandmeyer and benzyne mechanism
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.
synthon approach
1) The document discusses the synthon approach, which involves breaking down a target molecule into simpler starting materials through imaginary bond breaking (disconnection) or functional group interconversion.
2) Key terms are defined, including disconnection, synthon, and functional group interconversion. Basic rules of disconnection are outlined.
3) An example of using the synthon approach to synthesize the drug benzocaine from toluene is provided, outlining the multi-step reaction pathway and identifying specific synthons.
Michael addition reaction
The document discusses the Michael addition reaction, which involves the nucleophilic addition of a carbanion to an α,β-unsaturated carbonyl compound. It provides the definition, mechanism, examples including the synthesis of warfarin, and applications such as asymmetric Michael reactions. The mechanism involves deprotonation of the carbonyl compound by a base to form an enolate ion, which adds to the Michael acceptor to form a new carbon-carbon bond via 1,4-addition.
Brook rearrangement
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1) Wittig reagent is used to synthesize alkenes from ketones and aldehydes via the Wittig reaction. It is prepared from triphenylphosphine and alkyl halides.
2) Diazopropane is used for cyclopropanation of alkenes and is prepared by oxidation of acetohydrazone.
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Ugi Reaction
The document describes the Ugi reaction, a multi-component reaction where a ketone or aldehyde, amine, isocyanide, and carboxylic acid come together to form a bis-amide. It was first reported in 1959 by Ivar Karl Ugi. The reaction has high atom economy and yields, occurs rapidly at room temperature, and is uncatalyzed. It has applications in synthesizing chemical libraries and multiple compounds in one step, such as the HIV drug Crixivan. The mechanism involves imine formation, proton exchange, additions of the isocyanide and carboxylic acid, and a Mumm's rearrangement.
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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.
Suzuki reaction
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The document discusses functional group interconversions (FGIs) in organic synthesis. It defines FGIs as writing one functional group for another to help with retrosynthetic planning. FGIs are important for identifying suitable disconnections in retrosynthesis when a molecule contains multiple functional groups. The document categorizes common functional groups containing heteroatoms, such as carboxylic acids, aldehydes/ketones, and alcohols/amines. It also discusses methods for oxidizing and reducing functional groups, as well as removing functional groups altogether.
Ullmann reaction
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2. Key concepts include synthons, which are idealized fragments formed by imagined bond cleavages, and synthetic equivalents, which are actual reagents that can function as those synthons.
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1. The document discusses the basic concepts of retrosynthetic analysis in organic synthesis. Retrosynthesis is the process of working backward from a target molecule to design synthetic routes using disconnections and functional group interconversions.
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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.
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This document discusses several reagents used in organic synthesis:
1) Wittig reagent is used to synthesize alkenes from ketones and aldehydes via the Wittig reaction. It is prepared from triphenylphosphine and alkyl halides.
2) Diazopropane is used for cyclopropanation of alkenes and is prepared by oxidation of acetohydrazone.
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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.
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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.
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FGIs
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Ullmann reaction
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1. The document discusses the basic concepts of retrosynthetic analysis in organic synthesis. Retrosynthesis is the process of working backward from a target molecule to design synthetic routes using disconnections and functional group interconversions.
2. Key concepts include synthons, which are idealized fragments formed by imagined bond cleavages, and synthetic equivalents, which are actual reagents that can function as those synthons.
3. Effective retrosynthesis requires understanding reaction mechanisms and reliable reactions, as well as considering availability of starting materials and stereochemistry.
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DISCONNECTION-retrosynthesis.pptx
An approach for designing organic synthesis which involves breaking down of target molecule into available starting material by imaginary breaking of bonds (disconnection) and/or by functional group interconversion is known as disconnection approach or retrosynthesis or synthesis backward.
The C-X disconnection approach is mainly applicable to a carbon chain attached to any of the heteroatoms like O, N, or S. Here, a bond joins the heteroatom (X) to the rest of the molecule like a C-O, C-N, or C-S group. This point is good point to initiate a disconnection. This is called a ‘One-group’ C-X disconnection as one would need to identify only one functional group like ester, ether, amide etc. to make the disconnection.
How to choose a disconnection?
These are the few general strategy which are important points introduced which apply to the whole of synthetic design rather than one particular area. The main choice is between the various disconnection, even such a simple disconnection as the following alcohol can be disconnected.
We want to get back to simple starting materials and we shall do if we disconnect the bond which are:
Towards the middle of the molecule thereby breaking into two reasonably equal halves rather than chopping off one or two carbon atoms from the end and,
At a branch as this is more likely to give straight chain fragments and these are more likely to be available.
Disconnections very often take place immediately adjacent to, or very close to functional groups in the target molecule. This is pretty much inevitable, given that functionality almost invariably arises from the forward reaction.
A simple example is the weedkiller propanil used on rice fields. Amide disconnection gives amine obviously made from o-dichlorobenzene by nitration and reduction. All positions around the ring in o-dichlorobenzene are about the same electronically but steric hindrance will lead to dichloronitrobenzene being the major product
This compound was needed for some research into the mechanisms of rearrangements. We can disconnect on either side of the ether oxygen atom, but (b) is much better because (a) does not correspond to a reliable reaction: it might be hard to control selective alkylation of the primary hydroxyl group in the presence of the secondary one.
The disconnections we have made so far have all been of C–O, C–N, or C–S bonds, but, of course, the most important reactions in organic synthesis are those that form C–C bonds. We can analyze C–C disconnections in much the same way as we’ve analyzed C–X disconnections.
The Zeneca drug propranolol is a beta-blocker that reduces blood pressure and is one of the top drugs worldwide. It has two 1,2-relationships in its structure but it is best to disconnect the more reactive amine group first.
Arildone is a drug that prevents polio and herpes simplex viruses from ‘unwrapping’ their DNA, and renders them harmless.
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Retrosynthesis
Retrosynthetic analysis is a technique for planning organic syntheses by systematically deconstructing a target molecule into simpler precursor structures through disconnections, with the goal of arriving at commercially available starting materials. Key criteria for good disconnections include a favorable mechanism, maximizing simplification at each step, and producing recognizable starting materials. Common disconnections involve breaking bonds between functional groups like alcohols, alkenes, ketones, acids, and saturated/aromatic hydrocarbons. Protection and activation of reactive groups is sometimes required to control reaction selectivity. Proper application of retrosynthesis allows complex multi-step syntheses to be planned systematically and increases the likelihood of success.
Retrosynth.pdf
The document discusses retrosynthetic analysis, a technique used in organic synthesis planning. It involves deconstructing a target molecule into simpler precursor structures by applying the reverse of known reactions. This is done iteratively until commercially available starting materials are reached. Key points discussed include:
- Identifying functional groups and reactive sites ("retrons") that suggest disconnection points
- Applying topological and transform-based strategies to simplify the target structure
- Generating a retrosynthetic tree showing possible routes from precursors to the target
- Choosing disconnections that make the precursors easier to synthesize than the target
Synthon Approach ppt
This document discusses the synthon approach to retrosynthetic analysis in organic synthesis. It defines key terms like disconnection, synthon, and functional group interconversion. The document outlines basic rules for disconnection, such as generating stable fragments and minimizing the number of fragments. It provides guidelines for good retrosynthesis and discusses the use of synthons in the multi-step synthesis of benzocaine from toluene as an example.
Retrosynthesis by Professor Beubenz
For B Pharmacy and M Pharmacy Students
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physical chemistry is a one of th est field in chemical stuies
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2) Radical cross-coupling reactions allow forming C-C and C-X bonds through hydrogen atom transfer or coupling of radicals with redox-active esters, sulfones, or other species. This provides unique chemoselectivity advantages over polar pathways.
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Noise pollution can negatively impact human health and the environment. It is caused by loud sounds from sources like vehicles, construction sites, and industrial activity. Prolonged exposure to noise above safe levels can lead to hearing loss, cardiovascular issues, and disrupted sleep. Methods to reduce noise pollution include using barriers around noisy machinery, limiting vehicle speeds, planting trees as buffers, and protecting workers' hearing with earplugs. Controlling noise at the source is the most effective approach.
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Retro synthesis
- 2. Organic synthesis The preparation of a desired organic compound from a readily available starting material is known as organic synthesis. Synthesis- Singular Syntheses - Plural
- 3. • Compound which we wish to prepare is called a desired organic compound. • Hetero atoms are more electronegative O,Br,Cl,I etc. partial positive charge appears on carbon [+] • Si, Mg, Li are electropositive compound with the carbon, The polarity in this case is reversed partial negative charge on carbon [-]
- 4. Ideal synthesis Environment acceptance • Avoidance of problematic waste [ Green Route ] • Avoidance of toxic intermediate [ The Healthiest route ] • Atom economy
- 5. Safe- avoidance of risk procedure. Economically acceptable • Cost of materials –the cheapest route • Novelty – the patent route Robust- Easily scale up reproducibility. High efficient – Simple, high yield, a few steps.
- 6. The exercise of organic synthesis require •Knowledge of reactivity [ structure, Mechanism] •Design ability [ Retro synthetic Analysis]
- 7. The ultimate goal of organic synthesis is to assemble an organic compound from readily available starting material and reagents in the most efficient way. This process usually begins with the design of a synthetic plan.
- 8. Retro synthesis • The process of working backward from target molecule in order to device suitable synthetic route. Or • The process of mentally breaking down a molecule into a starting material.
- 9. Need for retrosynthesis • To attain shorter synthesis path for the target . • To increase yield of the process by choosing another synthesis strategy.
- 12. Disconnection • It is a paper operation involving an imagined cleavage of bond. • As a result of disconnection, usually positive and negative ion are formed which are called synthons. • It is shown by wavy line Or zigzag line
- 13. Disconnection
- 14. Functional Group Interconversion • Process of writing one functional group for another to help synthetic planning is known as Functional Group Interconversion. • It can be achieved by addition, substitution, elimination, oxidation, reduction and free radical reaction.
- 15. • Synthons are idealized fragments. • Synthons are shown by a + or – like anion or cation but not the real anion or cation. • Synthetic equivalent is denoted by a Is known as REAGENT
- 17. Rules for Disconnections • The hardest task in designing a retrosynthetic analysis is spotting where to make the disconnection. • Disconnection must correspond to known reliable reactions and it is the most important thing to bear in mind when working out a retro synthesis.
- 18. • For compounds consisting of two parts joined by hetero atom, disconnect next to the hetero atom.