Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products
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Springer-V erlag Wien GmbH
Prof. W. HERZ, Department of Chemistry, The Florida State Vniversity, Tallahassee, Florida, V.S.A. Prof. H. FALK, Institut fiir Chemie, Linz, Austria
Johannes-Kepler-Vniversităt,
Prof. G. W. KIRBY, Chemistry Department, The Vniversity of Glasgow, Glasgow, Scotland Prof. R. E. MOORE, Department of Chemistry, Vniversity of Hawaii at Manoa, Honolulu, Hawaii, V.S.A.
This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concemed, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks.
© 2000 by Springer-Verlag Wien Origina1ly published by Springer-Verlag I Wien in 2000 Softcover reprint ofthe hardcover lst edition 2000 Library of Congress Catalog Card Number AC 39-1015 Typesetting: Thomson Press (India) Ltd., New Delhi Graphic design: Ecke Bonk Printed on acid-free and chlorine-free bleached paper SPIN: 10743105
With 11 Figures
ISSN 0071-7886
ISBN 978-3-7091-7235-3 ISBN978-3-7091-6341-2(eBook) DOI 10.1007/978-3-7091-6341-2
Contents List of Contributors . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Synthetic Aspects of Iridoid Chemistry By H. FRANZYK . •.• •. •. •. • . • . .. . .
VII
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I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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2. Classification of Iridoids . . . . . . . . . . 2.1. Iridoid Glycosides . . . . . . . . . . . 2.2. Non-Glycosidic Iridoids . . . . . . . 2.3. Nitrogen-Containing Compounds .
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3. Availability and Production of Iridoids . 3.1. Plant Sources . . . . . . . . . . . . . . . 3.2. Cel1-Cultures. . . . . . . . . . . . . . . . 3.3. Isolation and Purification Methods.
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4. Semi-Synthetic Conversions Between Iridoids . . . . . . . . . . . . . . . 4.1. Hydrolysis and Lactonization . . . . . . . . . . . . . . . . . . . . . . . 4.2. Decarboxylation of Iridoid Glucosides . . . . . . . . . . . . . . . . . 4.3. Reduction and Oxidation of Iridoid Glucosides . . . . . . . . . . . 4.4. Miscel1aneous Transformations Used in Structure Elucidation . 4.5. Non-Glucosidic Iridoids . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.6. Ring-Cleavage Sequences and Sccoiridoid Chemistry . . . . . .
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5. Monoterpene Alkaloids Structural1y Rela
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