STEREOSPECIFIC TOTAL SYNTHESES OF DECAHYDROQUINOLINE ALKALOIDS (+/-)-195A AND (+/-)-2-EPI-195A

被引：72

作者：

POLNIASZEK, RP

DILLARD, LW

机构：

[1] Department of Chemistry, Duke University, Durham

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 15期

关键词：

D O I：

10.1021/jo00041a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total syntheses of decahydroquinoline alkaloids (+/-)-195A (pumiliotoxin C) and (+/-)-2-epi-195A are described. An unexpected, stereospecific epimerization of the C2 stereocenter of intermediate 6a occurred during its reduction. The isomerization resulted in ultimate production of 2-epi-195A. The stereochemical relationship of the C2, C4a, C5, and C8a stereocenters in 2-epi-195A is common to other decahydroquinoline alkaloids and gephyrotoxin. The 2-epi-195A synthesis demonstrated the viability of an N-Me group as a nitrogen protecting group. Alkaloid 195A was prepared in 5.0% overall yield by minor modification of the protocol established in the 2-epi-195A synthesis.

引用

页码：4103 / 4110

页数：8

共 48 条

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