Progress in the Chemistry of Organic Natural Products
Contents: Y. Asakawa: Chemical Constituents of the Bryophytes. 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 1
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Progress in the Chemistl7 of Organie Natural Produets
65 Founded ~ L Zeehmeister Edited ~ W. Harz, G. W. Kir~, R. E. Moore, W. Steelieh, Gnd Ch. ramm
Author: Y. Asakawa
Sprin,er-Verla, Wien NewYorJr IqqS
Prof. W. HERZ, Department of Chemistry, The Florida State University, Tallahassee, Florida, U.S.A. Prof. G. W. KIRBY, Chemistry Department, The University, Glasgow, Scotland Prof. R. E. MOORE, Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii, U.S.A. Prof. Dr. W. STEGLICH, Institut fUr Organische Chemie der Universitat Miinchen, Miinchen, Federal Republic of Germany Prof. Dr. CH. TAMM, Institut fUr Organische Chemie der Universitat Basel, Basel, Switzerland
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.
© 1995 by Springer-Vedag/Wien Softcover reprint of the hardcover 1st edition 1995 Library of Congress Catalog Card Number AC 39-1015 Typesetting: Macmillan India Ltd., Bangalore-25 Printed on acid-free and chlorine-free bleached paper
With 2 Figures
ISSN 0071-7886
ISBN-13:978-3-7091-7427-2 e-ISBN-13:978-3-7091-6896-7 DOl: 10.1007/978-3-7091-6896-7
Contents List of Contributors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . IX Chemical Constituents of the Bryophytes. By Y.
ASAKAWA.•
I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5 II. Chemical Constituents of Hepaticae (Liverworts) 12 1. Monoterpenoids . . . . 12 2. Tris-normonoterpenoids 15 3. Homomonoterpenoids . 15 4. Tris-norsesquiterpenoids 24 5. Sesquiterpenoids. . . . . 25 5.1 Acoranes and Noracoranes . .26 5.2 Africanes, Norafricanes and Secoafricanes . .27 5.3 Aristolanes. . . . . . . . . . . . . . . . 32 5.4 Aromadendranes, Secoaromadendranes and Norsecoaromadendranes . . . 33 5.5 Azulenes and Indenes . . . . .42 5.6 Barbatanes (Gymnomitranes) . .47 5.7 Bazzananes . . . . . . . . . .49 5.8. Bergamotanes, Bicyc10elemanes and Elemanes 51 5.9 Bicyc1ogermacranes, Isobicyc1ogermacranes and Lepidozanes . 54 5.10 Bisabolanes, Bourbonanes and Brasilanes . 57 5.11 Cadinanes, Amorphanes and Muurolanes . 60 . 61 5.12 Calamenanes, Calacoranes and Cadalenes . 5.13 Caryophyllanes, Cedranes and Chamigranes . 65 136 5.14 Chiloscyphanes, Oppositanes, Copaanes and Cubebanes 5.15 Cuparanes and Herbertanes (Isocuparanes) 140 5.16 Daucanes (Carotanes) and Drimanes 152 157 5.17 Eremophilanes and Eudesmanes 5.18 Farnesanes and Germacranes 171 5.19 Gorgonanes and Guaianes . . . 176 5.20 Himachalanes and Humulanes . 177 5.21 Longifolanes, Longibornanes, Longipinanes and Longicyc1anes 179 5.22 Maalianes and Monocyc1ofarnesanes . 182 5.23 Myltaylanes and Cyc10myltaylanes . 186 5.24 Pacifigorgianes and Patchoulanes 188 5.25 Pinguisanes and Norpinguisanes . . 190
VI
Contents
5.26 Santalanes, Spirovetivanes, Thujopsanes and Valencanes 5.27 Vitran
