Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstof

Naturally Occurring Cyclic Tetrapyrroles.- 1. Introduction.- 2. Classification.- 3. General Aspects of Cyclic Tetrapyrrole Biosynthesis.- 4. Porphyrins.- 4.1. Occurrence, Structure, and Biological Function.- 4.2. Biosynthesis.- 4.3. Aspects of Synthesis.- 5. Chlorins.- 5.1. Occurrence, Structure, and Biological Activity.- 5.2. Biosynthesis.- 5.3. Aspects of Synthesis.- 6. Bacteriochlorins.- 6.1. Occurrence, Structure, and Biological Activity.- 6.2. Aspects of Synthesis.- 7. Isobacteriochlorins.- 7.1. Occurrence, Structure, and Biological Activity.- 7.2. Biosynthesis.- 7.3. Aspects of Synthesis.- 8. Higher Saturated Hydroporphyrins.- 8.1. Occurrence, Structure, and Biological Activity.- 8.2. Biosynthesis.- 9. Corrins.- Acknowledgments.- References.- The Chemistry of Taxol and Related Taxoids.- 1. Introduction.- 2. A-Ring Chemistry.- 2.1. Modifications of the 11,12-Double Bond.- 2.2. Modifications at C-13.- 2.3. Modifications at C-14.- 2.4. Modifications at C-18.- 3. B-Ring Chemistry.- 3.1. Modifications at C-10.- 3.2. Modifications at C-9.- 3.3. Modifications at C-19.- 3.4. Modifications at C-2.- 3.5. Modifications at C-l.- 3.6. Other B-Ring Analogs.- 3.7. SAR of B-Ring Analogs.- 4. C-Ring Chemistry.- 4.1. The C-7 Hydroxyl Group.- 4.2. Products Derived from 6,7-Dehydrotaxol.- 4.3. Modifications at C-4.- 5. D-Ring Chemistry.- 5.1. Ring Opening by Electrophiles.- 5.2. Ring-Opening by Nucleophiles.- 5.3. D-Ring Analogs.- 5.4. Spectroscopic and Theoretical Studies.- 6. Rearrangements and Related Reactions.- 6.1. Rearrangements Leading to 11(15?1)-abeo taxols (A-nortaxols).- 6.2. Rearrangements Involving the B-Ring.- 6.3. Rearrangements Involving Both A- and B-Rings.- 6.4. Rearrangements of Ring C.- 7. The Side Chain.- 7.1. Synthesis of the Side Chain by the -lactam Approach.- 7.2. Synthesis of the Side Chain via an Epoxide Intermediate.- 7.3. Synthesis of the Side Chain by Sharpless Asymmetric Aminohydroxylation.- 7.4. Synthesis of the Side Chain by Coupling Reactions.- 7.5. Synthesis of Cyclically Protected Side Chains.- 7.6. Miscellaneous Syntheses.- 7.7. Syntheses of Phosphonate Side Chain Analogs.- 8. Synthesis of Taxol and Taxol Side Chain Analogs from Baccatin III.- 8.1. Synthesis of Taxol and Docetaxel.- 8.2. Synthesis of N-Acyl Analogs of Taxol.- 8.3. Synthesis of 3?-Aryl Analogs of Taxol.- 8.4. Taxol Analogs with Modified N-Acyl and 3?-Aryl Groups.- 8.5. Taxol Analogs Modified Both on the Side Chain and the Ring System.- 8.6. Synthesis of Taxol Analogs with Highly Modified Side Chains.- 8.7. Side Chain Chemistry.- 9. Taxol Metabolites.- 10. Taxol Analogs and Prodrugs.- 10.1. Simple Ester Derivatives and Prodrugs.- 10.2. Phosphate Ester and other Prodrugs.- 10.3. Taxol Analogs with Polymeric Acyl Substitutions.- 10.4. Targeted Analogs of Taxol.- 11. Labeled Taxol Analogs.- 11.1. Isotopically Labeled Taxols.- 11.2. Photoaffinity Labeled Taxols.- 11.3. Fluorescent and Other Labeled Taxols.- 12. The Synthesis of Taxol and Taxol Analogs from Precursors other than Baccatin III.- 13. The Synthesis of Simplified and Unusual Taxol Analogs.- 13.1. Simplified Analogs.- 13.2. Dimeric Analogs.- 14. The Synthesis of Taxol.- 14.1. The Holton Synthesis.- 14.2. The Nicolaou Synthesis.- 14.3. The Danishefsky Synthesis.- 14.4. The Wender Synthesis.- 14.5. The Kuwajima Synthesis.- 14.6. The Mukaiyama Synthesis.- 15. The Interaction of Taxol with Tubulin.- 15.1. Photoaffinity Labeling Studies.- 15.2. Fluorescence Spectroscopic Studies.- 15.3. Nuclear Magnetic Resonance Studies.- 15.4. The Taxol Pharmacophore.- Addendum.- Acknowledgements.- References.- Author Index.