Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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 relate

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L. Zechmeister Edited by W. Herz, H. Falk, G. W Kirby, and R. E. Moore Author: S. Huneck

Springer-Verlag Wien GmbH

Prof. W. Herz, Department of Chemistry, The Florida State University, Tallahassee, Florida, U. S. A. Prof. H. Falk, Institut für Chemie, Johannes-Kepler-Universität, Linz, Austria 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. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks. © 2001 by Springer-Verlag Wien Originally published by Springer-Verlag Wien New York 2001 Softcover reprint ofthe hardcover 1st edition 2001 Library of Congress Catalog Card Number AC 39-1015

Typesetting: Scientific Publishing Services (P) Ltd., Madras

Printed on acid-free and chlorine-free bleached paper SPIN: 10774546 With 11 Figures

ISSN 0071-7886

ISBN 978-3-7091-7249-0 ISBN 978-3-7091-6196-8 (eBook) DOI 10.1007/978-3-7091-6196-8

Contents List of Contributors

VIII

New Results on the Chemistry of Lichen Substances By S. Huneck

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Abbre viations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

4

I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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2. Methods for Identification and Structure Elucidation of Lichen Substances . . . .

5

2.1.

Spot Tests

2.2. Thin Layer Chromatography (TLC) . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3. 2.4. 2.5. 2.6. 2.7. 2.8.

High Performance Liquid Chromatography (HPLC) Droplet Counter-Current Chromatography . . . . . . . . . . . NMR Spectroscopy. . . . . . . . . . . . . . . . . . . . . . . . . . . . Mass Spectrometry . . . . . . . . . . . . . . . . . . . . . . . . . . . . X-ray Analysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Cathodoluminescence and X-ray Microanalysis . . . . . . . . 2.9. Laser Microprobe Mass Spectrometry (LAMMA) . . . . . . 2.10. Fluorescence Microscopy . . . . . . . . . . . . . . . . . . . . . . . . 2.11. Computer Program for Identification of Lichen Subst ances (WINTABOLITES)

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3. General Methods for Derivatization and Regeneration of Lichen Substances . ..

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12 12 13 14 15 15 15 16 16 16 17 17 17 18 18

3.1. Carboxyl Groups . . . . . . . . . . . . . . . . . . . 3.1.1. Meth ylation 3.1.2. Benzylation and Debenzylation 3.1.3. Carboxylation and Decarboxylation 3.2. Alcoholic and Phenolic Groups . . . . . . . . . 3.2.1. Acetylation . . . . . . . . . . . . . . . . . . . 3.2.2. Methylation and Demethylation . . . . 3.2.3