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.
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.
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.
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.
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: 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.
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.
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.
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.
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.
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.
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.
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3) Organoboranes are unstable and hydroboration involves coordination of BH3 to the alkene, allowing for stereospecific anti-Markovnikov addition
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