The Alkaloids: Chemistry and Biology 65 PDF
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THE ALKALOIDS Chemistry and Biology 65 VOLUME This page intentionally left blank THE ALKALOIDS Chemistry and Biology 65 VOLUME Edited by Geoffrey A. Cordell Evanston, Illinois Amsterdam(cid:2)Boston(cid:2)Heidelberg(cid:2)London(cid:2)NewYork(cid:2)Oxford Paris(cid:2)SanDiego(cid:2)SanFrancisco(cid:2)Singapore(cid:2)Sydney(cid:2)Tokyo ACADEMIC AcademicPressisanimprintofElsevier PRESS Academic Press isanimprint ofElsevier 84Theobald’sRoad,London WC1X 8RR,UK Radarweg 29,PO Box 211,1000AEAmsterdam,The Netherlands Linacre House,JordanHill,OxfordOX2 8DP,UK 30CorporateDrive, Suite400, Burlington, MA01803, USA 525BStreet, Suite1900, SanDiego, CA92101-4495, USA Firstedition 2008 Copyrightr2008Elsevier Inc.Allrights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher PermissionsmaybesoughtdirectlyfromElsevier’sScience&TechnologyRights DepartmentinOxford,UK:phone(+44)(0)1865843830;fax(+44)(0)1865853333; email: [email protected]. Alternatively you can submit your request online by visiting the Elsevier web site at http://www.elsevier.com/locate/ permissions, andselectingObtaining permission to useElsevier material Notice No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. Because of rapid advances in the medical sciences, in particular, independent verification of diagnoses and drug dosages should be made ISBN:978-0-12-374296-4 ISSN:1099-4831 ForinformationonallAcademicPresspublications visitourwebsiteatbooks.elsevier.com Printed andbound inUSA 0809101112 109 8 76 5 4 32 1 CONTENTS Contributors vii Preface ix CHEMISTRY AND BIOLOGY OF CARBAZOLE ALKALOIDS 1. Introduction 1 2. Occurrence, Isolation, and Structure Elucidation 3 I. CarbazoleAlkaloids fromHigher Plants 3 II. CarbazoleAlkaloids fromOtherSources 96 3. Biogenesis of Carbazole Alkaloids 159 I. CarbazoleAlkaloids fromHigher Plants 159 II. CarbazoleAlkaloids fromOtherSources 168 4. Biological and Pharmacological Activities of Carbazole Alkaloids 181 I. Anti-TumorActive Carbazoles 181 II. AntibioticCarbazoles 188 III. Anti-Viral Carbazoles 189 IV. Anti-InflammatoryCarbazoles 190 V. Anti-Malarial Carbazoles 191 VI. DiversePharmacologically Active Carbazoles 191 5. Chemistry of Carbazole Alkaloids 195 I. GeneralMethods forCarbazole Construction 195 II. Total SynthesesofCarbazole Alkaloids 210 6. Addendum 385 References 391 Cumulative Index of Titles 411 Subject Index 419 v This page intentionally left blank CONTRIBUTORS Hans-Joachim Kno¨lker, Department Chemie, Technische Universita¨t Dresden, Dresden, Germany Kethiri R. Reddy, Department Chemie, Technische Universita¨t Dresden, Dresden, Germany vii This page intentionally left blank PREFACE This is the latest volume in the series ‘‘The Alkaloids: Chemistry and Biology’’ and covers a group of alkaloids comprising the carbazole nucleus. Single-topic volumes inthisserieshavebeenrare,andthelastonediscussedantitumoralkaloidsandwas publishedasVolume25in1985.Thisisthefirstvolumededicatedtoasinglealkaloid structure type since Volume 8, which dealt with the monoterpene indole alkaloids over 40 years ago. Thisbackgroundplacesincontexthowsignificantthisremarkablyextensiveand exceptionally well-organized single volume review of the ‘‘Chemistry and Biology of CarbazoleAlkaloids’’by Kno¨lker and Reddy actuallyis.Itbrings together for thefirst time all of the alkaloids that have been isolated from plant, microbial, and marine sources, which possess, in any aspect of their structure, a carbazole nucleus. The alkaloids are reviewed from the detailed aspects of their structure elucidation, and for the first time an approach is offered with respect to an overall view of their biogenetic pathways, which differ substantially based on the further structural elementsofwhichthecarbazoleisacorefeature.Thesediscussionsarefollowedbya detailed exposition of how the significance of these alkaloids has been enhanced through the determination of several important, clinically relevant, biological properties. Finally, the authors offer a comprehensive presentation of the many syntheticapproachestothevariouscarbazolealkaloids,fromthesimplealkaloidsto the more complex alkaloids, including the bis-alkaloids. Geoffrey A. Cordell Evanston, Illinois, USA ix
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