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

ISBN-13: 9783709192528 / Angielski / Miękka / 2012 / 330 str.

S. V. Bhat; L. Minale; R. Riccio

Opis

Contents: Sujata V. Bhat: Forskolin and Congeners. - L. Minale, R. Riccio and F. Zollo: Steroidal Oligoglycosides and Polyhydroxysteroids from Echinoderms. - 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

Forskolin and Congeners.- I. Introduction.- II. Isolation and Structure Determination.- III. Botanical and Biogenetic Consideration.- IV. Chemistry of Forskolin.- i) Acylation and Alkylation Reactions.- ii) Oxidations and Reductions.- iii) Biological Oxidations.- iv) Isomerisation, Fragmentation and Rearrangements.- V. Synthesis of Forskolin.- i) Approaches to the AB Ring System of Forskolin.- Intramolecular Diels-Alder (IMDA) Strategy.- Intermodular Diels-Alder Strategy.- Intermolecular Nitrile Oxide Cycloaddition Approach.- Intramolecular Radical Mediated Cyclization Followed by Mukiyama Aldolization.- Intramolecular Michael-Aldol Condensation Strategy.- Intramolecular Olefin Cyclization.- ii) Approaches to the ABC Ring System of Forskolin.- iii) Total Synthesis of Forskolin.- Ziegler’s Approach.- Ikegami’s Approach.- Corey’s Approach.- VI. Biological Activities of Forskolin.- i) Activation of Adenylate Cyclase.- ii) Pharmacological Activities with Therapeutic Significance.- iii) Modulation of Membrane Transport Proteins.- iv) Effect on Cell Growth.- v) Other Utility.- VII. Structure Activity Correlations.- VIII. Concluding Remarks.- Acknowledgements.- References.- Additional References.- Steroidal Oligoglycosides and Polyhydroxysteroids from Echinoderms.- 1. Introduction.- 2. Steroidal Oligoglycosides from Asteroidea (Starfishes): General characteristics.- 2.1 Isolation Procedures.- 3. Asterosaponins.- 3.1 Spectroscopy.- 3.1.1 1H and 13C NMR spectra of the steroidal aglycones.- 3.1.2 1H and 13C-NMR spectra of the saccharide chains.- 3.1.3 FAB-Mass spectra.- 4. Cyclic Steroidal Glycosides.- 5. Glycosides of Polyhydroxysteroids.- 5.1 Spectroscopy.- 6. Glycosides of Steroid Phosphates.- 7. Polyhydroxysteroids.- 7.1 Spectroscopy.- 8. Steroidal Glycosides and Polyhydroxysteroids from Ophiuroidea (brittle stars).- 8.1 Spectroscopy.- 9. Assignment of Absolute Configurations to Stereogenic Carbons in the Side Chain of Polyhydroxysteroids.- 9.1 24-Hydroxysteroids.- 9.2 26-Hydroxysteroids.- 9.3 24-Hydroxymethylsteroids.- 9.4 24-(ß-Hydroxyethyl)- and 24-(Carboxymethyl)steroids.- 9.5 24-Methyl-26-hydroxy- and 24-methyl-26-oic Steroidal side-chains.- 9.6 24-Ethyl-26-hydroxysteroids.- 9.7 24-Methyl-25,26-dihydroxysteroids.- Acknowledgements.- Name Index of Asterosaponins.- Molecular Weight Index of Asterosaponins.- Name Index of Polyhydroxysteroid, Glycosides.- Molecular Weight Index of Polyhydroxy steroid Glycosides.- Name Index of Polyhydroxysteroids.- Molecular Weight Index of Polyhydroxysteroids.- References.- Author Index.