A novel route to the geissoschizine skeleton: The influence of ligands on the diastereoselectivity of the Heck cyclization

被引:35
作者
Birman, VB [1 ]
Rawal, VH [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
D O I
10.1016/S0040-4039(98)01591-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise, novel route to the geissoschizine skeleton has been developed. The key step involves a Heck cyclization reaction, which was found to lead to opposite diastereomers, (+/-)-8 or (+/-)-9, depending on the reaction conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7219 / 7222
页数:4
相关论文
共 24 条
[1]  
BANKS BJ, 1981, J TETRAHEDRON LETT, V22, P1631
[2]   A concise, stereoselective synthesis of (+/-)-geissoschizine [J].
Bennasar, ML ;
Jimenez, JM ;
Sufi, BA ;
Bosch, J .
TETRAHEDRON LETTERS, 1996, 37 (50) :9105-9106
[3]   THERMODYNAMICALLY CONTROLLED STEREOSELECTIVE SYNTHESIS OF GEISSOSCHIZINE [J].
BENSON, W ;
WINTERFELDT, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (11) :862-863
[4]  
BOHLMANN C, 1985, LIEBIGS ANN CHEM, P1752
[5]   THE TOTAL SYNTHESIS OF (+/-)-C-MAVACURINE [J].
CALVERLEY, MJ ;
BANKS, BJ ;
HARLEYMASON, J .
TETRAHEDRON LETTERS, 1981, 22 (17) :1635-1638
[6]  
HECK RF, 1982, ORG REACTIONS, V27, P345
[7]   GEISSOSCHIZOL IN PESCHIERA-LAETA [J].
JAHODAR, L ;
VOTICKY, Z ;
CAVA, MP .
PHYTOCHEMISTRY, 1974, 13 (12) :2880-2881
[8]   HECK-TYPE REACTIONS IN WATER [J].
JEFFERY, T .
TETRAHEDRON LETTERS, 1994, 35 (19) :3051-3054
[9]   Short synthetic route to (+/-)-geissoschizine [J].
Lounasmaa, M ;
Jokela, R ;
Anttila, U ;
Hanhinen, P ;
Laine, C .
TETRAHEDRON, 1996, 52 (19) :6803-6810
[10]   NEW, SHORT SYNTHESIS OF (+/-)-GEISSOSCHIZINE [J].
LOUNASMAA, M ;
JOKELA, R ;
MIETTINEN, J ;
HALONEN, M .
HETEROCYCLES, 1992, 34 (08) :1497-1502