ASYMMETRIC TOTAL SYNTHESIS OF TACAMONINE (PSEUDOVINCAMONE-I) VIA RADICAL CYCLIZATION

被引：43

作者：

IHARA, M ^{[1
]}

SETSU, F ^{[1
]}

SHOHDA, M ^{[1
]}

TANIGUCHI, N ^{[1
]}

TOKUNAGA, Y ^{[1
]}

FUKUMOTO, K ^{[1
]}

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 98077,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 18期

关键词：

D O I：

10.1021/jo00097a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-{N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).

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页码：5317 / 5323

页数：7

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