Organic Synthetic Methods

Synthesis is one of the major endeavours of the organic chemist, and the design of a successful synthesis requires a sound knowledge of functional group chemistry, stereochemistry and organic reaction mechanisms.Organic Synthetic Methods introduces the major methods of creating carbon-carbon and carbon-nitrogen bonds, along with functional group interconversions (Oxidation, reduction, halogenation). The use of protecting groups and solid-phase methods are also discussed. The analysis of the structure of a target molecule, in terms of the structural consequences of synthetic reactions, is introduced to enable the student to identify key dissections and building blocks and hence develop a suitable synthetic method. Examples of the synthesis of labelled compounds are also provided.

James R. Hanson is Professor in the Department of Chemistry at the University of Sussex.

Introduction	p. 1
Synthetic Strategies	p. 1
Steric Factors	p. 3
Criteria for Evaluating Synthetic Routes	p. 3
Some Synthetic Terms	p. 6
Learning to Apply Synthetic Methods	p. 6
Organometallic and Ylide Methods of Carbon-Carbon Bond Formation	p. 9
Introduction	p. 9
Reactions of Organometallic Compounds	p. 11
Acetylides and Nitriles	p. 20
Ylide Reactions	p. 22
Silicon and Boron in C-C Bond Formation	p. 26
Carbonyl Activation and Enolate Chemistry in Carbon-Carbon Bond Formation	p. 32
Introduction	p. 32
Alkylation Reactions	p. 36
Enolate Anions in Carbonyl Addition Reactions	p. 39
The Stereochemistry of Condensation Reactions	p. 48
Carbocations in Synthesis	p. 54
Introduction	p. 54
Alkyl Carbocations: the Friedel-Crafts Alkylation	p. 55
Carbocations Derived from Aldehydes and Ketones	p. 56
Acylium Carbocations: the Friedel-Crafts Acylation	p. 57
Acid-catalysed Rearrangement Reactions	p. 58
Free Radical and Pericyclic Reactions in the Formation of Carbon-Carbon Bonds	p. 64
Carbon Radical Reactions	p. 64
Radical Addition Reactions	p. 68
Carbenes	p. 69
Alkene Metathesis	p. 70
The Diels-Alder Reaction	p. 71
The Ene Reaction	p. 73
The Cope and Claisen Rearrangements	p. 73
Methods of Making Carbon-Nitrogen Bonds	p. 78
Introduction	p. 78
Electrophilic Methods of Making C-N Bonds	p. 79
Nucleophilic Methods of Making C-N Bonds	p. 80
Rearrangement Methods	p. 84
The Synthesis of Amino Acids	p. 85
The Synthesis of Heterocyclic Compounds	p. 87
Functional Group Transformations	p. 96
Oxidation	p. 96
Reduction	p. 103
Halogenation	p. 111
Protecting Groups	p. 126
Protection of Functional Groups	p. 126
Peptide Synthesis	p. 133
Combinatorial Synthesis	p. 136
Some Examples of Total Syntheses	p. 142
Introduction	p. 142
[beta]-Eudesmol	p. 143
Griseofulvin	p. 144
Thiamine (Vitamin B[subscript 1])	p. 147
Prostaglandins	p. 150
Further Reading	p. 153
Answers to Problems	p. 157
Subject Index	p. 173
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Organic Synthetic Methods

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