ENANTIOSELECTIVE TOTAL SYNTHESES OF INDOLIZIDINE ALKALOIDS 167B AND 209D

被引：136

作者：

POLNIASZEK, RP

BELMONT, SE

机构：

[1] Paul M. Gross Chemical Laboratories, Department of Chemistry, Duke University, North Carolina 27706, Durham

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 15期

关键词：

D O I：

10.1021/jo00302a038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective total syntheses of the indolizidine alkaloids 167B and 209D are described. The syntheses proceed via a common late-stage intermediate, amino nitrile 8. Each alkaloid was prepared in 10 steps and approximately 23% overall yield from (S)-(-)-α-phenethylamine. The configurations of these materials were determined by a combination of one- and two-dimensional NMR experiments. © 1990, American Chemical Society. All rights reserved.

引用

页码：4688 / 4693

页数：6

共 40 条

[1] AARON HS, 1968, TETRAHEDRON LETT, P6191
[2] [Anonymous], COMMUNICATION
[3] INTERACTION OF GEPHYROTOXIN AND INDOLIZIDINE ALKALOIDS WITH THE NICOTINIC ACETYLCHOLINE RECEPTOR-ION CHANNEL COMPLEX OF TORPEDO ELECTROPLAX
ARONSTAM, RS
DALY, JW
SPANDE, TF
NARAYANAN, TK
ALBUQUERQUE, EX
[J]. NEUROCHEMICAL RESEARCH, 1986, 11 (08) : 1227 - 1240
[4] HYDROZIRCONATION .2. OXIDATIVE HOMOLOGATION OF OLEFINS VIA CARBON-MONOXIDE INSERTION INTO CARBON-ZIRCONIUM BOND
BERTELO, CA
SCHWARTZ, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (01) : 228 - 230
[5] CORRELATION OF PROTON AND C-13 NMR-SPECTRA BY HETERONUCLEAR 2-DIMENSIONAL SPECTROSCOPY
BODENHAUSEN, G
FREEMAN, R
[J]. JOURNAL OF MAGNETIC RESONANCE, 1977, 28 (03) : 471 - 476
[6] LUPINEN-ALKALOIDE .8. ZUR KONFIGURATIONSBESTIMMUNG VON CHINOLIZIDIN-DERIVATEN
BOHLMANN, F
[J]. CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (10): : 2157 - 2167
[7] 2-CYANO DELTA-3 PIPERIDEINES .8. BIOMIMETIC APPROACH TO THE SYNTHESIS OF THE DECAHYDROQUINOLINE RING-SYSTEM OF POISON-DART FROG TOXINS
BONIN, M
BESSELIEVRE, R
GRIERSON, DS
HUSSON, HP
[J]. TETRAHEDRON LETTERS, 1983, 24 (14) : 1493 - 1496
[8] 2-CYANO DELTA-3 PIPERIDINES .6. A GENERAL-METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CIS AND TRANS 2,6-DIALKYLPIPERIDINE ALKALOIDS
BONIN, M
ROMERO, JR
GRIERSON, DS
HUSSON, HP
[J]. TETRAHEDRON LETTERS, 1982, 23 (33) : 3369 - 3372
[9] 2-CYANO-DELTA-3-PIPERIDEINES .12. STEREOCHEMISTRY OF FORMATION OF N-BENZYL-2-CYANO-DELTA-3-PIPERIDEINES AND FACILE ISOMERIZATION ON ALUMINA TO 2-CYANO-DELTA-4-PIPERIDEINES - A POTENTIALLY GENERAL-ROUTE TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINE ALKALOIDS
BONIN, M
ROMERO, JR
GRIERSON, DS
HUSSON, HP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (13) : 2392 - 2400
[10] A SHORT SYNTHESIS OF (+/-)-GEPHYROTOXIN 223AB
BRANDI, A
CORDERO, F
QUERCI, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1748 - 1750

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