Organic Synthetic Methods

1.1 Synthetic Strategies.

1.2 Steric Factors.

1.3 Criteria for Evaluating Synthetic Routes.

1.4 Some Synthetic Terms.

1.5 Learning to Apply Synthetic Methods.

2. Organometallic and Ylide Methods of carbon-Carbon Bond Formation.

2.1 Introduction.

2.2 Reactions of Organometallic Compounds.

2.3 Acetylides and Nitriles.

2.4 Ylide Reactions.

2.5 Silicon and Boron in C-C Bond Formation.

3. Carbonyl Activation and Enolate Chemistry in Carbon-Carbon Bond Formation.

3.1 Introduction.

3.2 Alkylation Reactions.

3.3 Enolate Anions in Carbonyl Addition Reactions.

3.4 The Stereochemistry of Condensation Reactions.

4. Carbocations in Synthesis.

4.1 Introduction.

4.2 Alkly Carbocations: The Friedel-Crafts Alkylation.

4.3 Carbocations Derived from Aldehydes and Ketones.

4.4 Acylium Carbocations: The Friedel-Crafts Acylation.

4.5 Acid-catalysed Rearrangement Reactions.

5. Free Radical and Pericyclic Reactions in the Formation of Carbon-Carbon Bonds.

5.1 Carbon Radical Reactions.

5.2 Radical Addition Reactions.

5.3 Carbenes.

5.4 Alkene Metathesis.

5.5 The Diels-Alder Reaction.

5.6 The Ene Reaction.

5.7 The Cope and Claisen Rearrangements.

6. Methods of Making Carbon-Nitrogen Bonds.

6.1 Introduction.

6.2 Electrophilic Methods of Making C-N Bonds.

6.3 Nucleophilic Methods of Making C-N Bonds.

6.4 Rearrangements Methods.

6.5 The Synthesis of Amino Acids.

6.6 The Synthesis of Heterocyclic Compounds.

7. Functional Group Transformations.

7.1 Oxidation.

7.2 Reduction.

7.3 Halogenation.

8. Protecting Groups.

8.1 Protection of Functional Groups.

8.2 Peptide Synthesis.

8.3 Combinatorial Synthesis.

9. Some Examples of Total Synthesis.

9.1 Introduction.

9.2 β-Eudesmol.

9.3 Griseofulvin.

9.4 Thiamine (Vitamin B₁).

9.5 Prostaglandins.

Further Reading.

Answers to Problems.

Subject Index.