The Alkaloids: Chemistry and Pharmacology 36

351 Pages·1990·10.2 MB·English

by  Arnold Brossi (Eds.)

THE ALKALOIDS
Chemistry and Pharmacology
VOLUME 36
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THE ALKALOIDS
Chemistry and Pharmacology
Edited by
Arnold Brossi
Narionul Instirures of Health
Bethesda, Maryland
VOLUME 36
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I’KINItil) IN 11111 LINl’ltU STAIES 01- AMI;KICA
XY ‘If1 ‘)I 92 <I x 7 h r J 3 2 I
CONTENTS
CONTRIBUTO.R.S.. ...................................................... ix
PREFAC.E. .............................................................. xi
Chapter I. Alkaloids of Slwchnos and Gardneria Species
NORIOA IMI,S HIN-ICHIRSOA KAAI,N D YOSHIOB AN
I. Introduction ...................................................... I
11. Srrychnos Alkaloids ............................................... 2
111. Gardneria Alkaloids ............................................... 47
IV. Pharmacology of Gardneria Alkaloids. ............................... 62
References ....................................................... 62
Chapter 2. Lead Tetraacetate Oxidation in Alkaloid Synthesis
OSAMUH OSHINOAN D BUNSUKUEM EZAWA
I. Introduction ............. 70
11. Aporphines ....................................................... 72
111. C-Homoaporphines.. ...... 83
IV. Homoproaporphines ............................................... 90
V. Morphinandienones and Homomorphinandienones .................... 91
VI. Isopavines and Homoisopavines .... 94
VII. Benzo[c]phenanthridines ........................................... 95
96
IX. Tetrahydroprotoberberines ................... 97
X. Indole Alkaloids ................................................... 98
XI. Oxoaporphines. ............................ I10
XII. Lead Tetraacetate-Mediated Hydroxylation of lsoquin Ill
XIII. Miscellaneous Reactions ..................................... 126
............................ 130
V
vi CONTENTS
Chapter 3. Canthin-6-one Alkaloids
TAlCHl OHMOTO AND KAZUOK OIKE
I. Introduction ...................................................... 135
11. Natural Occurrence. .................. 136
111. Structural Elucidation ............................... I37
1V. "C-NMR Spectroscopy ..... ....................... 154
V. Synthesis .................. I55
VI. Biosynthesis.. ............. ....................... 164
V11. Bioassay and Pharmacology . ....................... I65
References . .................................... 167
Chapter 4. Phenethylisoquinoline Alkaloids
TETSUJl KAMETAN1 AND MASUOK OlZLlMl
1. Introduction ...................................................... 172
II. Structural Elucidation, Chemical Reaction, and Stereochemistry of
Phenethylisoquinoline Alkaloids. .................................... 173
Ill. Biosynthesis ............... ....................... 200
IV. Synthesis.. ................ ..... 202
V. Pharmacology ........................ 219
References ................ ....................... 220
Chapter 5. Alkaloids of the Calabar Bean
SEIICHI TAKANOAN D KUNlO OCASAWARA
I. Introduction ...................................................... 225
11. Structures of the Alkaloids ......................................... 225
111. Synthesis of the Alkaloids .......................................... 226
IV. Pharmacology ..................................................... 247
References ....................................................... 249
Chapter 6. Chemistry of Melanins
RAIMONDCOR IPPA, VACLAV HORAKG, IUSEPPEPR OTA, PARIS SVORONOS, AND
LESZEKW OLFRAM
I. Introduction ...................................................... 254
11. Natural Melanins.. ................................................ 256
Ill. Synthetic Melanins ................................................ 268
IV. Isolation, Purification, and Characterization .......................... 279
V. Structure and Chemical Properties.. ................................. 283
CONTENTS vii
VI. Spectroscopic Characterization ..................................... 297
Appendix ......................................................... 307
References ....................................................... 3 12
CUMULATIIVNED EX OF TITLES.. ........... .... 325
INDEX .................................... 33 I
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CONTRIBUTORS
Numbers in parentheses indicate the pages on which the author’s contributions begin.
NORIOA IMI( I), Faculty of Pharmaceutical Sciences, Chiba University,
Chiba 260, Japan
YOSHIOB AN( I), Hokkaido University, Sapporo 060, Japan
RAIMONDCOR IPPA(2 53), University of Parma, Parma, Italy
VACLAVH ORAK(2 53), Georgetown University, Washington, D.C. 20057
OSAMUH OSHINO(6 9), Faculty of Pharmaceutical Sciences, Science Uni-
versity of Tokyo, 12, Shinjuku-ku, Tokyo 162, Japan
TETSUJKI AMETAN(I1*7 1), Institute of Medicinal Chemistry, Hoshi Uni-
versity, Tokyo, Japan
KAZUOK OIKE( 139, School of Pharmaceutical Sciences, Toho Univer-
sity, Chiba 274, Japan
MASUOK OIZUM(I1 71), Fujigotemba Research Laboratories, Research
Management Department, Chugai Pharmaceutical Co. Ltd., Toshi-
moku, Tokyo 171, Japan
KUNIOO GASAWAR(2A2 5), Pharmaceutical Institute, Tohoku University,
Aobayama, Sendai 980, Japan
TAICHOI HMOTO(1 33, School of Pharmaceutical Sciences, Toho Univer-
sity, Chiba 274, Japan
GIUSEPPPER OTA(2 53), Universita di Napoli, Napoli, Italy
SHIN-ICHIRSOA KA(II ), Faculty of Pharmaceutical Sciences, Chiba Uni-
versity, Chiba 260, Japan
PARISS VORONO(2S5 3), Queensborough College of the City University of
New York, Bayside, New York I1364
SEIICHTI AKANO(2 25), Pharmaceutical Institute, Tohoku University,
Aobayama, Sendai 980, Japan
BUNSUKUEM EZAWA(*6 9), Department of Pharmaceutical Sciences, Sci-
ence University of Tokyo, Shinjuku-ku, Tokyo, Japan
LESZEKW OLFRAM(2 53), Clairol Company, Stamford, Connecticut 06922
* Deceased
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