ENANTIOSELECTIVE SYNTHESIS OF (5R,9R)-5-PROPYL-OCTAHYDROINDOLIZINE [(-)-GEPHYROTOXIN 167B]

被引:36
作者
FLEURANT, A [1 ]
CELERIER, JP [1 ]
LHOMMET, G [1 ]
机构
[1] UNIV PARIS 06,CHIM HETEROCYCLES LAB,CNRS,URA 455,4 PL JUSSIEU,F-75252 PARIS 05,FRANCE
关键词
D O I
10.1016/S0957-4166(00)80503-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A versatile and practical synthesis of the dendrobatid alkaloid 167B is described using a chiral amino acid as starting material.
引用
收藏
页码:695 / 696
页数:2
相关论文
共 13 条
[1]   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
[2]  
Daly J. W., 1986, ALKALOIDS CHEM BIOL, V4, P1
[3]   FURTHER CLASSIFICATION OF SKIN ALKALOIDS FROM NEOTROPICAL POISON FROGS (DENDROBATIDAE), WITH A GENERAL SURVEY OF TOXIC NOXIOUS SUBSTANCES IN THE AMPHIBIA [J].
DALY, JW ;
MYERS, CW ;
WHITTAKER, N .
TOXICON, 1987, 25 (10) :1023-1095
[4]   STEREOSELECTIVE SYNTHESIS OF (+/-)-INDOLIZIDINES 167B, 205A, AND 207A - ENANTIOSELECTIVE SYNTHESIS OF (-)-INDOLIZIDINE 209B [J].
HOLMES, AB ;
SMITH, AL ;
WILLIAMS, SF ;
HUGHES, LR ;
LIDERT, Z ;
SWITHENBANK, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1393-1405
[5]   SHORT, ENANTIOGENIC SYNTHESES OF (-)-INDOLIZIDINE 167B AND (+)-MONOMORINE [J].
JEFFORD, CW ;
TANG, Q ;
ZASLONA, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (09) :3513-3518
[6]  
LIONS F, 1940, J P R SOC NSW, V73, P240
[7]   HIGHLY DIASTEREOSELECTIVE ALKYLATION OF CHIRAL TIN(II) ENOLATES ONTO CYCLIC ACYL IMINES - AN EFFICIENT ASYMMETRIC-SYNTHESIS OF BICYCLIC ALKALOIDS BEARING A NITROGEN ATOM RING JUNCTURE [J].
NAGAO, Y ;
DAI, WM ;
OCHIAI, M ;
TSUKAGOSHI, S ;
FUJITA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1148-1156
[8]   SULFUR TRIOXIDE IN OXIDATION OF ALCOHOLS BY DIMETHYL SULFOXIDE [J].
PARIKH, JR ;
DOERING, WVE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5505-&
[9]   ENANTIOSELECTIVE TOTAL SYNTHESES OF INDOLIZIDINE ALKALOIDS 167B AND 209D [J].
POLNIASZEK, RP ;
BELMONT, SE .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4688-4693
[10]   SYNTHESES OF (S)-5-SUBSTITUTED 4-AMINOPENTANOIC ACIDS - NEW CLASS OF GAMMA-AMINOBUTYRIC ACID TRANSAMINASE INACTIVATORS [J].
SILVERMAN, RB ;
LEVY, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (05) :815-818