Enantiospecific synthesis of optically active 6-methoxytryptophan derivatives and total synthesis of tryprostatin A

被引：56

作者：

Gan, T ^{[1
]}

Liu, RY ^{[1
]}

Yu, P ^{[1
]}

Zhao, S ^{[1
]}

Cook, JM ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Milwaukee, WI 53201 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 26期

关键词：

D O I：

10.1021/jo971640w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise preparation of optically active L or D-6-methoxytryptophan ethyl ester 21 was developed via the Fischer indole/Schollkopf protocol from 6-methoxy-3-methylindole 16 (four steps, 58% overall yield). This method was extended to the enantiospecific total synthesis of tryprostatin A (11) via a regiospecific bromination process as a key step. In addition, 6-methoxy-2-bromotryptophan ethyl ester (32), a potential intermediate for indole alkaloid synthesis, was prepared via this strategy.

引用

页码：9298 / 9304

页数：7

共 48 条

[1] TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS .2. A CONVENIENT SYNTHESIS OF TRYPTAMINES AND BETA-CARBOLINES [J].