Alkaloids: Chemical and Biological Perspectives, Vol. 14

561 Pages·1999·15.75 MB·English

by  S. William Pelletier (Ed.)

Alkaloids: Chemical
and Biological
Perspectives
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Major Reference Works
BARTON, NAKANISHI, METH-COHN: Comprehensive Natural Products Chemistry
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KATRITZKY, REES & SCRIVEN: Comprehensive Heterocyclic Chemistry II
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BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
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Alkaloids: Chemical
and Biological
Perspectives
Volume Fourteen
Edited by
S. William Pelletier
Institute for Natural Products Research
and
Department of Chemistry
The University of Georgia, Athens
1999
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First edition 1999
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Transferred to digital printing 2006
Dedicated to
the memory of
Roger Adams
(1889-1971)
Roger Adams was one of the great leaders who influenced the development of chemistry in
the United States. He was born on June 2, 1889 (Boston), a member of the famous family
which produced two presidents of the United States. After graduation (B.A., 1905) he
obtained his Ph.D. (1912, Harvard) and spent three years (1913-1916) as an instructor in
the Chemistry Department of Harvard University. During this period he spent some time in
Germany to work with Richard Willstatter on the synthesis of some pyrrolomethanes re-
lated to the structure of chlorophyll. After returning from Germany, he joined the faculty
of the University of Illinois in Urbana (1916) and served as chairman of the chemistry de-
partment from 1926-1954.
Adams was interested in the study of natural products and established the correct structure
of the pyrroloquinazoline alkaloid vasicine (1936). He contributed largely to the study of
alkaloids of the Crotalaria and Senecio species which cause liver cirrhosis in grazing cattle.
Other pyrrolidine alkaloids studied by him were: monocrotaline, seneciphylline, retror-
sine, trichodesmine, jacobine and grantianine. He determined the structures of the "necic
acids" such as monocrotic and monocrotalic acids, and the bases isolated by hydrolysis of
the pyrrolidine alkaloids. He corrected the structure of riddellic acid, obtained by hydrol-
ysis of riddelliine, an alkaloid from Senecio riddellii. Adams worked on the structures of
gossypol from cotton seed meal, cannabinols from marijuana, and chalmoogra oil. He
worked for three decades on the stereochemistry of molecules with restricted rotations
about a single bond.
Adams's contributions to the growth of organic chemistry are extraordinary. He published
425 papers, guided 184 Ph.D. students, 50 postdoctorals and consulted for many major
chemical companies. Adams was solely responsible for starting the series of volumes of
Organic Syntheses (1921) and later Organic Reactions (1942).
B. S. Joshi
v
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Contributors
Toh-Seok Kam, Department of Chemistry, University of Malaya, 50603 Kuala Lumpur,
MALAYSIA.
Jie Jack Li, Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company,
2800 Plymouth Road, Ann Arbor, Michigan 48105, U.S.A.
Paul L. Schiff, Jr., Department of Pharmaceutical Sciences, School of Pharmacy,
University of Pittsburgh, Pennsylvania 15261, U.S.A.
vii
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Preface
Volume 14 of this series presents three interesting reviews of research on alkaloids. Chapter
1, by Paul L. Schiff, Jr. is a monumental effort, presenting a selective, comprehensive tabular
review of research on the bisbenzylisoquinoline alkaloids, with an analysis of the respective
alkaloid types. The chapter should serve as a very useful tool for the bench research scientist who
is involved in the isolation and elucidation of structures of bisbenzylisoquinoline alkaloids.
Moreover, the data in these tables provides the botanical distribution and occurrence (family,
genus, species) of the various classes of these alkaloids. The alkaloids are also categorized by
their molecular weights and structural types.
Chapter 2, by Toh-Seok Kam is a review of alkaloids derived from Malaysian flora.
Malaysia's position near the Equator confers on it a tropical climate characterized by high
temperatures, humidity, and rainfall, conditions favorable for plant life that has resulted in a rich
flora of about 15,000 species of higher plants. This review concentrates on work published during
the past twenty years and where appropriate compares the occurrence of alkaloids with studies of
similar plants from countries neighboring to Malaysia, especially Thailand and Indonesia.
Chapter 3 by Jie Jack Li presents a collection of very interesting total syntheses of naturally
occurring indole alkaloids where palladium chemistry plays a central role in the syntheses. Five
different types of palladium-mediated reactions are treated: (1) oxidative cyclization reactions
promoted by palladium (II) species; (2) transmetallation reactions with organoboranes,
organostannanes, and organozinc reagents; (3) inter- and intramolecular Heck reactions; (4)
reactions with 7t-allylpalladium as the intermediate; and (5) reactions using C-N bond formation as
the key step for the synthesis.
Each chapter in this volume has been reviewed by at least one specialist in the field. The edi-
tor thanks these reviewers for their important contributions to this volume. Indexes for both
subjects and organisms are provided.
The editor invites prospective contributions to write him about topics for review in future
volumes of this series.
S. William Pelletier
Athens, Georgia
July 15, 1998
IX