Total syntheses of five indole alkaloids from the marine bryozoan Flustra foliacea

被引：60

作者：

Morales-Ríos, MS ^{[1
]}

Suárez-Castillo, OR ^{[1
]}

Trujillo-Serrato, JJ ^{[1
]}

Joseph-Nathan, P ^{[1
]}

机构：

[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 04期

关键词：

D O I：

10.1021/jo0012647

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, efficient, and conceptually new approach to the total syntheses of marine-derived indole alkaloids, including (+/-)-flustramines A (I) and B (2), (+/-)-flustramides A (3) and B (4), and (+/-)-debromoflustramine B (5), is outlined. The key step in the syntheses involves the conjugated addition of an organomagnesium species derived from prenyl bromide to 2-hydroxyindolenines. Compounds 1. 2, and 5 have been synthesized in five steps with 23%, 17%, and 16% overall yield, respectively, whereas flustramides 3 and 4 have been synthesized in only four steps with 24% and 18% overall yield, respectively, on the basis of 2-hydroxyindolenines.

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页码：1186 / 1192

页数：7

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