The Alkaloids: Chemistry and Biology 65

441 Pages·2008·3.56 MB·English

by  Geoffrey A. Cordell (Eds.)

THE ALKALOIDS
Chemistry and Biology
65
VOLUME
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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
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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
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CONTRIBUTORS
Hans-Joachim Kno¨lker, Department Chemie, Technische Universita¨t Dresden,
Dresden, Germany
Kethiri R. Reddy, Department Chemie, Technische Universita¨t Dresden, Dresden,
Germany
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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