1. Synthetic Design
1.1 Retrosynthetic Design
1.2 Reversal of the Carbonyl Group Polarity (Umpolung)
1.3 Steps in Planning a Synthesis
1.4 Choice of Sythetic Method
1.5 Domino Reactions
1.6 Computer-Assisted Retrosynthetic Analysis
2. Stereochemical Considerations in Planning Synthesis
2.1 Conformational Analysis
2.2 Evaluation of Nonbonded Interactions
2.3 Six-Member Hetercyclic Systems
2.4 Polycyclic Ring Systems
2.5 Cyclohexyl Systems with sp2-Hybridized Atoms
2.6 Significant Energy Difference
2.7 Computer-Assisted Molecular Modeling
2.8 Reactivity and Product Determination as a Function of Conformation
3. The Concept of Protecting Functional Groups
3.1 Protection of NH Groups
3.2 Protection of OH Groups of Alcohols
3.3 Protection of Diols as Acetals
3.4 Protection of Carbonyl Groups in Aldehydes and Ketones
3.5 Protection of the Carboxyl Group
3.6 Protection of Double Bonds
3.7 Protection of Triple Bonds
4. Functional Group Transformations: Oxidation and Reduction
4.1 Oxidation of Alcohols to Aldehydes and Ketones
4.2 Reagents and Procedures of Alcohol Oxidation
4.3 Chemoselective Agents for Oxidizing Alcohols
4.4 Oxidation of Acyloins
4.5 Oxidation of Tertiary Allylic Alcohols
4.6 Oxidative Procedures to Carboxylic Acids
4.7 Allylic Oxidation of Alkenes
4.8 Terminology for Reduction of Carbonyl Compounds
4.9 Nucleophilic Reducing Agents
4.10 Electrophilic Reducing Agents
4.11 Regio- and Chemoselective Agents
4.12 Diastereoselective Reductions of Cyclic Ketones
4.13 Inversion of Secondary Alcohol Stereochemistry
4.14 Diastereofacial Selectivity in Acyclic Systems
4.15 Enantioselective Reductions
5. Functional Group Transformations: The Chemistry of Carbon-Carbon pi-Bonds and Related Reactions
5.1 Reactions of Carbon-Carbon Double Bonds
5.2 Reactions of Carbon-Carbon Triple Bonds
6. Formation of Carbon-Carbon Single Bonds
6.1 1,3-Dicarbonyl and Related Compounds
6.2 Direct Alkylation of Simple Enolates
6.3 Cyclization Reactions--Baldwin's Rules for Ring Closure
6.4 Stereochemistry of Cyclic Ketone Alkelation
6.5 Imine and Hydrazone Anions
6.6 Enamines
6.7 The Aldol Reaction
6.8 Condensation Reactions of Enols and Enolates
6.9 Robinson Annulation
7. Formation of Carbon-Carbon Bonds Via Organometallic Reagents
7.1 Organolithium Reagents
7.2 Organomagnesium Reagents
7.3 Organotitanium Reagents
7.4 Organocerium Reagents
7.5 Organocopper Reagents
7.6 Organochromium Reagents
7.7 Organozinc Reagents
7.8 Organoboron Reagents
7.9 Organosilicon Reagents
7.10 Palladium-Catalyzed Coupling Reactions
8. Formation of Carbon-Carbon pi-Bonds
8.1 Formation of Carbon-Carbon Double Bonds
8.2 Formation of Carbon-Carbon Triple Bonds
9. Synthesis of Carbocyclic Systems
9.1 Intramolecular Free Radical Cyclizations
9.2 Cation-pi Cyclizations
9.3 Pericyclic Reactions
9.4 Ring-Closing Olefin Metathesis (RCM)
10. The Art of Synthesis
Abbreviations
Answers to Select End-of-Chapter Problems
Index