Workbook for Organic Synthesis: The Disconnection Approach

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Edition: 2nd
Format: Hardcover
Pub. Date: 2010-01-11
Publisher(s): Wiley
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Summary

One approach to organic synthesis is retrosynthetic analysis. With this approach chemists start with the structures of their target molecules and progressively cut bonds to create simpler molecules. Reversing this process gives a synthetic route to the target molecule from simpler starting materials. This "disconnection" approach to synthesis is now a fundamental part of every organic synthesis course.Workbook for Organic Synthesis: The Disconnection Approach, 2 nd EditionThis workbook provides a comprehensive graded set of problems to illustrate and develop the themes of each of the chapters in the textbook Organic Synthesis: The Disconnection Approach, 2 nd Edition. Each problem is followed by a fully explained solution and discussion. The examples extend the student's experience of the types of molecules being synthesised by organic chemists, and the strategies they employ to control their syntheses. By working through these examples students will develop their skills in analysing synthetic challenges, and build a toolkit of strategies for planning new syntheses. Examples are drawn from pharmaceuticals, agrochemicals, natural products, pheromones, perfumery and flavouring compounds, dyestuffs, monomers, and intermediates used in more advanced synthetic work. Reasons for wishing to synthesise each compound are given. Together the workbook and textbook provide a complete course in retrosynthetic analysis.Organic Synthesis: The Disconnection Approach, 2 nd EditionThere are forty chapters in Organic Synthesis: The Disconnection Approach, 2 nd Edition: those on the synthesis of given types of molecules alternate with strategy chapters in which the methods just learnt are placed in a wider context. The synthesis chapters cover many ways of making each type of molecule starting with simple aromatic and aliphatic compounds with one functional group and progressing to molecules with many functional groups. The strategy chapters cover questions of selectivity, protection, stereochemistry, and develop more advanced thinking via reagents specifically designed for difficult problems. In its second edition updated examples and techniques are included and illustrated additional material has been added to take the student to the level required by the sequel, Organic Synthesis: Strategy and Control. Several chapters contain extensive new material based on courses that the authors give to chemists in the pharmaceutical industry.Workbook for Organic Synthesis: The Disconnection Approach, 2 nd edition, combined with the main textbook, provides a full course in retrosynthetic analysis for chemistry and biochemistry students, and a refresher course for organic chemists working in industry and academia.

Author Biography

Dr Stuart Warren Department of Chemistry, University of Cambridge, UK

Dr Warren is the author of the bestselling textbooks "Organic Synthesis: The Disconnection Approach" (Wiley), "Organic Synthesis: Strategy and Control" (Wiley) and "Organic Chemistry" (OUP)

Dr Paul Wyatt

School of Chemistry, University of Bristol, UK

Dr Wyatt is Director of Undergraduate Studies for the School of Chemistry at Bristol University and also Director of BRISTOL ChemLabS - a HEFCE Centre for Excellence in Teaching & Learning.?He is co-author, with Warren, of "Organic Synthesis: Strategy and Control"

Table of Contents

Preface
General References
The Disconnection Approach
Basic Principles: Synthons and Reagents Synthesis of Aromatic Compounds
The Order of Events
One-Group C-X Disconnections
Chemoselectivity
Two-Group C-X Disconnections
Reversal of Polarity, Cyclisations, Summary of Strategy
Amine Synthesis
Protecting Groups
One Group C-C Disconnections I: Alcohols
General Strategy A: Choosing a Disconnection
Stereoselectivity A
One Group C-C Disconnections II: Carbonyl Compounds
Regioselectivity
Alkene Synthesis
Use of Acetylenes (Alkynes)
Two-Group C-C Disconnections I: Diels-Alder Reactions
Introduction to Carbonyl Condensations
Two-Group C-C Disconnections II: 1,3-Difunctionalised Compounds
Control of Carbonyl Condensations
Two-Group C-C Disconnections III: 1,5- Difunctionalised Compounds Conjugate (Michael) Addition and Robinson Annelation
Aliphatic Nitro Compounds in Synthesis
Two Group Disconnections IV: 1,2- Difunctionalised Compounds
Radical Reactions in Synthesis
Two-Group Disconnections V: 1,4- Difunctionalised Compounds
Reconnection
Two-Group C-C Disconnections VI: 1,6-diCarbonyl Compounds
General Strategy B: Strategy of Carbonyl Disconnections
Introduction to Ring Synthesis: Saturated Heterocycles
Three-Membered Rings
Rearrangements in Synthesis
Four-Membered Rings: Photochemistry in Synthesis
The Use of Ketenes in Synthesis
Five-Membered Rings
Pericyclic Reactions in Synthesis: Special Methods for Five-Membered Rings
Six-Membered Rings
General Strategy C: Strategy of Ring Synthesis
Stereoselectivity B
Aromatic Heterocycles
General Strategy D: Advanced Strategy
Index
Table of Contents provided by Publisher. All Rights Reserved.

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