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 [J].

ARONSTAM, RS ;

DALY, JW ;

SPANDE, TF ;

NARAYANAN, TK ;

ALBUQUERQUE, EX .

NEUROCHEMICAL RESEARCH, 1986, 11 (08) :1227-1240

[4] HYDROZIRCONATION .2. OXIDATIVE HOMOLOGATION OF OLEFINS VIA CARBON-MONOXIDE INSERTION INTO CARBON-ZIRCONIUM BOND [J].

BERTELO, CA ;

SCHWARTZ, 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 [J].

BODENHAUSEN, G ;

FREEMAN, R .

JOURNAL OF MAGNETIC RESONANCE, 1977, 28 (03) :471-476

[6] LUPINEN-ALKALOIDE .8. ZUR KONFIGURATIONSBESTIMMUNG VON CHINOLIZIDIN-DERIVATEN [J].

BOHLMANN, F .

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 [J].

BONIN, M ;

BESSELIEVRE, R ;

GRIERSON, DS ;

HUSSON, HP .

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 [J].

BONIN, M ;

ROMERO, JR ;

GRIERSON, DS ;

HUSSON, HP .

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 [J].

BONIN, M ;

ROMERO, JR ;

GRIERSON, DS ;

HUSSON, HP .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (13) :2392-2400

[10] A SHORT SYNTHESIS OF (+/-)-GEPHYROTOXIN 223AB [J].

BRANDI, A ;

CORDERO, F ;

QUERCI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1748-1750

← 1 2 3 4 →