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123.312 Retrosynthesis: Lecture 3
The document discusses the benefits of exercise for mental health. Regular physical activity can help reduce anxiety and depression and improve mood and cognitive functioning. Exercise causes chemical changes in the brain that may help protect against mental illness and improve symptoms for those who already suffer from conditions like depression and anxiety.
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123.312 Retrosynthesis: Lecture 3
The document discusses the benefits of exercise for mental health. Regular physical activity can help reduce anxiety and depression and improve mood and cognitive functioning. Exercise causes chemical changes in the brain that may help protect against mental illness and improve symptoms for those who already suffer from conditions like depression and anxiety.
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The document discusses the benefits of exercise for mental health. Regular physical activity can help reduce anxiety and depression and improve mood and cognitive function. Exercise causes chemical changes in the brain that may help protect against mental illness and improve symptoms.
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The document discusses the benefits of exercise for mental health. Regular physical activity can help reduce anxiety and depression and improve mood and cognitive functioning. Exercise causes chemical changes in the brain that may help protect against mental illness and improve symptoms.
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The document discusses the benefits of exercise for mental health. Regular physical activity can help reduce anxiety and depression and improve mood and cognitive functioning. Exercise causes chemical changes in the brain that may help protect against mental illness and improve symptoms.
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123.312 Retrosynthesis: Lecture 2
The document discusses the benefits of exercise for mental health. Regular physical activity can help reduce anxiety and depression and improve mood and cognitive functioning. Exercise causes chemical changes in the brain that may help protect against mental illness and improve symptoms.
Basic Concepts Of Retrosynthesis (Part1)
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.
123.312 Retrosynthesis: Lecture 4
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Retrosynthesis: 123.312
This is an experiment. It is NOT a presentation. It is meant to be an interactive pdf for students to work through/revise from at their own pace. For these features to operate I guess it needs to be downloaded first.
It is based on 123.312 lectures on retrosynthesis or the design of chemical syntheses.
Organic synthesis the disconnection approach by stuart warren
This document is the table of contents for the book "Organic Synthesis: The Disconnection Approach" by Stuart Warren and Paul Wyatt. It lists the chapter titles for the book, which cover various strategies and approaches for organic synthesis such as disconnections involving C-X bonds, protection of functional groups, carbon-carbon bond formation, and multi-step reactions. The book is in its second edition and is intended to teach methods for planning retrosynthetic analyses of organic compounds.
Lecture6: 123.312
Lecture 6: C-C bond formation
The big one; the all important formation of C-C bonds. Reagents include organometallics and enolates. There will also be a slight detour into the wonderful world of pKa.
Lecture7: 123.312
Told you that this was the important one. This weeks reagents include more enolates and then reactions with the C=O group including the such classics as the Wittig reaction.
Basic Concepts Of Retrosynthesis (Part 2)
The document discusses retrosynthetic analysis approaches for synthesizing 1-phenylhexanol. It presents 6 different retrosynthetic disconnections and proposed syntheses, considering factors like availability of reagents and minimizing synthetic steps. The best synthesis is the one that uses readily available reagents and fewest steps, while breaking carbon-carbon bonds in the center of the molecule.
Lecture1: 123.312
This document outlines the contents of a book on functional group interconversions. It covers topics like alcohols, carboxylic acids and their derivatives, oxidation and reduction reactions, and C-C bond formation. Each chapter explains different reaction types and transformation pathways. The introduction discusses using natural products for medical treatments historically and the importance of functional group interconversions in organic synthesis.
Lecture2: 123.312
This document discusses functional group interconversions, specifically focusing on sulfonate esters. It provides information on common sulfonate leaving groups like tosyl, mesyl, and triflate groups and their relative reactivities. It also discusses the mechanisms and standard methods for preparing sulfonate esters from alcohols using these strong acidic leaving groups, noting that pyridine cannot deprotonate an alcohol directly due to pKa differences.
Lecture5: 123.312
Finishing oxidation by looking at the Baeyer-Villiger reaction and then turning our attention to reduction. Once again we will see the usual suspects with a who is who of hydride sources.
Lecture3: 123.312
A brief look at alcohol protecting groups and then an introduction to carboxylic acid derivatives. Start of the reactions of carboxylic acids.
Problems 1 answers
1. The document describes several organic reactions and asks questions about determining product structures and rationalizing stereochemical outcomes.
2. Key concepts discussed include: conformational analysis to determine reactivity; Cram chelation control to set stereochemistry; Ireland-Claisen rearrangements maintaining configuration; and using chiral auxiliaries to induce diastereoselectivity through chelation.
3. Rationalizations of stereochemical outcomes involve analyzing transition states, identifying favored conformations, and determining approach selectivity based on steric interactions.
Lecture8: 123.312
The document provides information about various carbon-carbon bond forming reactions including the aldol reaction, Claisen condensation, Dieckmann cyclization, Robinson annulation, and the Hajos-Parrish-Eder-Sauer-Wiechert reaction. It discusses how to control the chemoselectivity of reactions and outlines strategies like choosing the correct nucleophile or pre-forming enolates. Functional groups in specific arrangements like a 1,3-diol relationship indicate certain reaction types. The key message is that retrosynthesis involves recognizing underlying patterns in molecular structures.
Lecture4: 123.312
Finishing off the reactions of carboxylic acid derivatives (well the substitution reactions) and introducing oxidation and reduction. Then looking at the oxidation of alkenes (epoxidation and dihydroxylation) and alcohols (the usual suspects).
Tutorial 1 answers
The document describes several reactions involving conjugate additions and discusses the stereochemical outcomes. It rationalizes the stereoselectivity using concepts like chair conformations, Felkin-Anh control, and Cram chelation control. By analyzing the transition states and preferred conformations, it is able to explain why the reactions favor one stereoisomer over another in each case.
Lecture3 123713B
An introduction to total synthesis and retrosynthesis. A quick overview of retrosynthesis followed by one of the many syntheses of (–)-stenine. This is just an overview of the fascinating world of organic synthesis, it is not intended to teach retrosynthesis or organic synthesis. For that see some of my other lecture notes.
Problems 2 answers
More problems covering asymmetric synthesis. This time with examples of substrate control, chiral reagents, and chiral catalysis. Also another example of a synthesis.
Lecture2 123713A
Chiral catalysis. This is a relatively brief look at some classic examples of chiral catalysis in organic synthesis. It gives a quick overview but does not go into any detail.
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123713AB lecture10
A look at epothilone A as it includes examples of many different forms of asymmetric synthesis. Also includes a little bit about ring-closing metathesis.
123713AB lecture09
Synthesis of hirsutene.
Here because I love the use of radicals in synthesis (and yes, this lecture includes a quick re-cap of radical chemistry).
123713AB lecture08
This document summarizes MacMillan's total synthesis of callipeltoside C, which employs organocatalysis and several interesting chemical transformations. The retrosynthesis splits the molecule into three fragments - the macrocyclic lactone core, carbohydrate, and a third segment prepared using organocatalysis. The forward synthesis couples these fragments in a convergent manner, with key steps including a Negishi carbometallation, organocatalytic hydroxylation, Semmelhack reaction to form the tetrahydropyran ring, and glycosidation to join the sugar moiety. The synthesis highlights the utility of retrosynthesis in simplifying complex targets and total synthesis in confirming the structure of natural products.
123713AB lecture07
Gives an introduction to total synthesis and why we do it (which reminds me, I must add a picture of Everest, as I think the fact that 'it is there' is the main reason for most syntheses). Then to introduce the topic with a reasonably simple synthesis, we will look at an example of the synthesis of Tamiflu.
123713AB lecture06
This document discusses organocatalysis, which uses small organic molecules rather than metals to catalyze chemical reactions. It notes the benefits of organocatalysis such as robust catalysts, new reaction types, and cleaner chemistry. Specific examples are provided of reactions catalyzed by proline, imidazolidinones, thioureas, and phosphoric acids. These catalysts form reactive intermediates like enamines and iminium ions to activate substrates for nucleophilic attack. Overall, organocatalysis is presented as a useful tool for synthetic chemists to address issues like solvent use, purification, and atom economy.
123713AB lecture05
This is the biggy, the one everyone wants to achieve. Here we will be looking at metal-based chiral catalysis. We will concentrate on bisoxazoline-based Lewis acid catalysis and then look at reductions before finishing with the ubiquitous Sharpless epoxidation and dihydroxylation.
123713AB lecture04
Use of stoichiometric amounts of a chiral source. The usual suspects will be discussed, including borane reagents (mostly pinene derivatives) and the Brown allylation.
123713AB lecture03
Self explanatory really, this lecture looks at chiral auxiliaries. We will concentrate on oxazolidinones in alkylations, aldol reaction and the Diels-Alder reaction. There will be a couple examples of other auxiliaries.
123713AB lecture02
1) The document discusses various methods of substrate control in organic reactions, focusing on how substrate conformation can influence diastereoselectivity. Allylic 1,3-strain (A1,3 strain), where substituents on the first and third carbons interact sterically, is a key concept.
2) Reactions like epoxidation and hydroboration are often highly diastereoselective when the substrate adopts a conformation that positions the smallest substituent syn to the reactive double bond to minimize A1,3 strain. The reagent then approaches from the least hindered face.
3) Directed reactions use hydrogen bonding or coordination to deliver the reagent to one
123713AB lecture01
General introduction to the course followed by a basic introduction to asymmetric or stereoselective Synthesis. Then starting the course proper by looking at substrate control.
Tutorial 3 answers
The document discusses the total synthesis of ibuprofen and the antihypertensive drug valsartan from starting materials.
For ibuprofen, a retrosynthetic analysis is performed to arrive at reactions to connect the starting materials in the forward sense. For valsartan, a retrosynthesis is proposed using a carboxylic acid starting material and an amine.
Lastly, a retrosynthesis is proposed for an asymmetric molecule shown, dividing it into two subunits that can be synthesized and coupled using reactions like Mitsunobu, Brown allylation/crotylation, and peptide coupling.
Tutorial 2 answers
The second set of tutorial questions on asymmetric synthesis. This one covers chiral reagents and starts enantioselective catalysis.
Lecture4 123713B
This document summarizes the synthesis of the anti-cancer compound epothilone A. It discusses the retrosynthesis of epothilone C and the synthesis of the required fragments - C1-C6, C7-C12, and C13-C21. These fragments were coupled and the ring was formed using ring-closing metathesis. Finally, epothilone C was converted to the target compound epothilone A through oxidation and reduction reactions. The synthesis utilized substrate-controlled aldol reactions, Sharpless asymmetric dihydroxylation, and ring-closing metathesis to construct the molecule with high stereoselectivity.
Lecture1 123713A
The document discusses various topics related to chirality and stereochemistry including:
- Different forms that can exhibit chirality beyond just tetrahedral stereocenters.
- The relationship between enantiomers, diastereomers, and meso compounds for molecules with multiple stereocenters.
- How purity of chiral compounds is measured in terms of enantiomeric excess and ratio, and diastereomeric excess and ratio.
- Common methods for determining enantiomeric excess such as derivatization reactions and chiral chromatography.
Organic chemistry and stereoisomers
These slides are part of a talk to school teachers. They were designed to showcase some of the applications of organic chemistry, the range of natural and synthetic products. I'm not sure how much use it is without my commentary but, as always, it seems a waste to leave it on my hard drive. The second half gave a overview of chirality and stereoisomers as this topic often causes problems with students. This second half owes a lot to an excellent paper by Robert Gawley (J. Chem. Ed. 2005, 82, 1009) and just has prettier papers. This version of the talk includes a section I removed when presenting (due to time) on artificial sweeteners.
Muconin
123.713A/B. Description of the Jacobsen synthesis of muconin. This is an example of total synthesis, retrosynthesis and asymmetric synthesis and shows the kind of information required in the assigment for this course.
123.202 Lecture 11 - alkynes
This document provides a summary of dienes and alkynes. It discusses resonance stabilization of conjugated dienes and their regioisomers when undergoing electrophilic addition. For alkynes, it covers their lack of acidity due to their sp hybridization and decreasing acid strength. It also summarizes the hydration of alkynes, which proceeds by a Markovnikov addition through a mercurinium ion intermediate and tautomerizes to the enol form.
123.202 Lecture 10 - alkenes
The lecture discusses the mechanisms of ozonolysis and radical addition reactions to alkenes. Ozonolysis involves a three step mechanism where ozone cleaves the alkene to form an ozonide intermediate which then decomposes to a carbonyl compound. Radical addition reactions involve a three step chain reaction mechanism of initiation, propagation, and termination. The stability of radical intermediates is influenced by resonance stabilization, which explains why styrene reacts with HBr to give a single, benzylic bromide product.
123.202 Lecture 9 - alkenes
This document summarizes reactions of alkenes including:
1. Addition of bromine to form bromonium ions and give anti-addition of bromine with stereospecificity.
2. Diol formation from epoxide ring opening, KMnO4 oxidation, and hydroboration-hydration which can give stereospecific or racemic mixtures.
3. Examples of biologically active natural products formed from alkene reactions like epothilones and dynemicin A.
123.202 Lecture 8 - alkenes
The document summarizes key concepts about alkene reactions:
1) Markovnikov addition results in the addition occurring on the carbon with the most hydrogen substituents, giving the more substituted primary carbocation which is most stable.
2) Hydroboration follows anti-Markovnikov addition, with the BH3 group adding to the less substituted carbon. Oxidation then occurs with H2O2/NaOH through a 1,2-shift to give anti-Markovnikov addition.
3) Organoboranes are unstable and hydroboration involves coordination of BH3 to the alkene, allowing for stereospecific anti-Markovnikov addition