The total synthesis of (-)-suaveoline

被引：36

作者：

Bailey, PD ^{[1
]}

Morgan, KM ^{[1
]}

机构：

[1] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 21期

关键词：

D O I：

10.1039/b005695m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of the indole alkaloid (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%). Key synthetic steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons and alkylation procedure, a vinylogous Thorpe cyclisation and the direct formation of a 3,4,5-trisubstituted pyridine from a 1,5-dinitrile. The direct conversion of ajmaline to semi-synthetic suaveoline is also described.

引用

页码：3578 / 3583

页数：6

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