Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products
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L. Zechmeister Edited by
w. Herz, H. Falk, G. W. Kirby, and R. E. Moore Authors: C. W. J. Chang, H. Greger, and o. Hofer
Springer-Verlag Wien GmbH
Prof. W. Herz, Department of Chemistry, The Florida State University, Tallahassee, Florida, U. S. A. Prof. H. Falk, Institut fiir Chemie, Linz, Austria
Johannes-Kepler-Universităt,
Prof. G. W. Kirby, Chemistry Department, The University of Glasgow, Glasgow, Scotland Prof. R. E. Moore, Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii, U. S. A.
This work is subject to copyright. AII rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of iIIustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks. © 2000 by Springer-Verlag Wien Originally published by Springer-Verlag Wien New York in 2000 Softcover reprint of the hardcover 1st edition 2000 Library ofCongress Catalog Card Number AC 39-1015
Typesetting: Scientific Publishing Services (P) Ltd., Madras
Graphic design: Ecke Bonk Printed on acid-free and chlorine-free bleached paper SPIN: 10763781 With 2 Figures
ISSN 0071-7886
ISBN 978-3-7091-7238-4 ISBN 978-3-7091-6331-3 (eBook) DOI 10.1007/978-3-7091-6331-3
Contents List of Contributors.
. .................... VIII
Naturally Occurring Isocyano/Isothiocyanato and Related Compounds By C. W. 1. Chang . . .. . . .. . . ........ . . . . .. . . .. .. . . .. . . . ....... . I. Introduction 1.1. Occurrence and Distribution . . . .. .. . . .. . ............. . 1.2. Nomenclature and Structural Representation . . . . . . . . . . . . . . . . 1.3. Isolation and Identification . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.3.1. Physical and Chemical Properties ................ . 1.3.2. Spectral Characterization 2. Monoterpene Indole Alkaloids from Blue-Green Algae ....... . 2.1. Cel-Compounds . . . ........ . . ...... . 2.1.1. Hapalindolcs . . . . . . . . . . . . . . . 2.1.1.1. Tetracydic Hapalindoles . . . . . . . . . . . . . . . . . . . . ........... . 2.1.1.2. Tricyclic Hapalindoles . ......... . 2.1.2. Fischcrindolcs . . . . . . . . . . . . . . . 2.2. Oxindoles and Modified Oxygenated Cel-Indoles . 2.2.1. Hapaloxindoles . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.2.2. Hapalonamidcs . . . . . . . . . . . 2.2.3. Hapalindolinones 2.2.4. Welwitindolinoncs 2.3. Ce,,-Indolc Alkaloids. 2.3.1. Ambiguinc Isonitrilcs 2.4. Reactions of Hapalindoics . 2.5. Syntheses of Hapalindoics 3. Marine Diterpenes from Sponges . . . . . . . . . 3.1. Acyclics . . . . . . . . . . . . . . . . . . . . . . . . 3.2. Kalihinancs .. . . .. . . . . .. . . . . .. . . .. . . . ........ . 3.2. I. Kalihinols from Al'lIlli/ll'lIl1 Sponges ......... . ....... . 3.2.2. Tetrahydropyrans ............. . 3.2.3. Tetrahydrofurans . ........ . 3.2.4. Dihydropyrans . . . . . . . . ................. . 3.3. Amphilectanes 3.3.1. Isocyanoditerpencs from Crmhllsi£'/a /lOoperi ............. . 3.3.2. Amphilcctanes. . .....
