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

ISBN-13: 9783709192443 / Angielski / Miękka / 2012 / 206 str.

D. G. I. Kingston; A. A. Molinero; J. M. Rimoldi

Opis

Contents: D. G. I. Kingston, A. A. Molinero, and J. M. Rimoldi: The Taxane Diterpenoids. - Author Index. - Subject Index. The volumes of this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Spis treści

The Taxane Diterpenoids.- 1. Introduction.- 2. General Structural Characteristic and Nomenclature.- 3. The Families of Taxane Diterpenoids.- 3.1. Taxoids with a C-4(20) Exocyclic Double Bond.- 3.2. Taxoids with a C-4(20) Epoxide.- 3.3. Taxoids with an Oxetane Ring.- 3.4. Miscellaneous Taxoids.- 4. The Chemistry of the Taxoids.- 4.1. Isolation Techniques.- 4.1.1. Extraction.- 4.1.2. Purification and Analysis.- 4.2. Spectroscopy.- 4.2.1. UV and ORD/CD Spectroscopy.- 4.2.2. Infrared Spectroscopy.- 4.2.3. 1H-NMR Spectroscopy.- 4.2.4. 13C-NMR Spectroscopy.- 4.2.5. Mass Spectrometry.- 4.2.6. X-ray Crystallography.- 4.3. Chemical Reactivity.- 4.3.1. Acylation and Other Protective Group Chemistry.- 4.3.2. Hydrolysis.- 4.3.3. Epimerization at C-7.- 4.3.4. Oxidation.- 4.3.5. Reduction.- 4.3.6. Rearrangements and Related Reactions.- 4.3.7. Photochemistry.- 5. Approaches to the Synthesis of Taxane Diterpenoids.- 5.1. Linear Strategies.- 5.1.1. Biomimetic Approaches.- 5.1.1.1. Kato’s Approach.- 5.1.1.2. Frejd’s Approach.- 5.1.1.3. Pattenden’s Approach.- 5.1.2. Intramolecular Diels-Alder Approaches.- 5.1.2.1. Shea’s Approach..- 5.1.2.2. Jenkin’s Approach.- 5.1.2.3. Sakan’s Approach.- 5.1.2.4. Yadav’s Approach.- 5.1.3. AB?ABC Approaches.- 5.1.3.1. Martin’s Approach.- 5.1.3.2. Holton’s Approaches: The Synthesis of Taxusin.- 5.1.3.3. Oishi’s Approach.- 5.1.3:4. Fetizon’s Second Approach.- 5.1.3.5. Blechert’s Second Approach.- 5.1.3.6. Wender’s C-Ring Annulation Approach.- 5.1.3.7. Kraus’ Approach.- 5.1.3.8. Yamada’s Approach.- 5.1.3.9. Fetizon’s Third Approach.- 5.1.3.10. Gadwood’s Approach.- 5.1.4. BC?ABC Approaches.- 5.1.4.1. Swindell’s Approach.- 5.1.4.2. Wender’s A-Ring Annulation Approach.- 5.1.4.3. Sieburth’s Approach.- 5.1.4.4. Kanematsu’s Approach.- 5.2. Convergent Strategies.- 5.2.1. AC?ABC Approaches.- 5.2.1.1. Kitagawa’s Approach.- 5.2.1.2. Fetizon’s First Approach.- 5.2.1.3. Kende’s Approach.- 5.2.1.4. Funk’s Approach.- 5.2.1.5. Kuwajima’s Approach.- 5.2.2. A[B]C?ABC Approaches.- 5.2.2.1. Trost’s Approach.- 5.2.2.2. Inouye’s First Approach.- 5.2.2.3. Blechert’s First Approach.- 5.2.2.4. Clark’s Approach.- 5.2.2.5. Berkowitz’s Approach.- 5.2.2.6. Inouye’s Second Approach.- 5.2.2.7. Winkler’s Approach.- 5.2.2.8. A Variation on Fetizon’s Second Approach.- 5.2.2.9. Ghosh’s Approach.- 5.2.2.10. Paquette’s Approach.- 5.2.2.11. Snider’s Approach.- 5.2.2.12. Zucker’s Approach.- 5.2.2.13. Frejd’s Synthesis of a Secotaxoid.- 5.3. Partial Synthesis of Taxol and Related Compounds.- 5.3.1. Synthesis of Taxol and Taxol Analogues from 13-innamoylbaccatin III.- 5.3.2. Synthesis of Taxol by Acylation of Baccatin III with a Pre-formed Side Chain.- 5.3.3. Acylation of Baccatin III with (3-Lactams or Oxazinones.- 5.3.4. Synthesis of Taxol Analogues.- 5.3.5. Synthesis of Oxetane Models.- 6. Biosynthesis and Biotransformation of Taxoids.- 6.1. Biosynthesis of Taxoids.- 6.2. Biotransformation of Taxoids.- 7. Bioactivity of Taxol and Other Taxoids.- 7.1. Toxicity of Taxus Alkaloids.- 7.2. Biological Activity of Taxol and Related Compounds.- 7.2.1. Antitumor Activity of Taxol.- 7.2.2. Microtubule Assembly Activity of Taxol.- 7.2.3. Structure-activity Relationships of Taxol Analogs.- Addendum.- Acknowledgements.- References.- Author Index.