Progress in the Chemistry of Organic Natural Products / Fortschritte Der Chemie Organischer Naturstoffe

ISBN-13: 9783709132289 / Angielski / Miękka / 2012 / 253 str.

Glasenapp-Breiling, M.

Opis

The first contribution of this book gives an overview on naturally occuring cycling tetrapyrroles. The article describes the four classic tetrapyrrolic structures with their porphyrin, chlorin, bacteriochlorin and corrin skeletons and also novel, interesting structures with unusual biological activities. This review mainly focuses on the occurrence, structure and biological function as well as biosynthesis and aspects of synthesis. The second article deals with the anticancer compound taxol and its semisynthetic analog docetaxel (Taxotere). Taxol was originally isolated in the late 1960s on the basis of its cytotoxity and antileukemic activity, its structure was published in 1971 in a paper that has been cited 1000 times since this publication. The review focuses primarily on the interesting and novel chemistry of taxol that has been discovered over the last eight years."

Spis treści

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.