A Diastereoselective Total Synthesis of trans-Trikentrin A: A Ring Contraction Approach

被引：48

作者：

Silva, Luiz F., Jr. ^{[1
]}

Craveiro, Marcus V. ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim, BR-05513970 Sao Paulo, Brazil

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 23期

关键词：

D O I：

10.1021/ol8023105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route to obtain the polyalkylated indole (+/-)-trans-trikentrin A was developed. The synthesis of this natural alkaloid features a thallium(III)mediated ring contraction reaction to obtain the trans-1,3-disubstituted five-membered ring in a diastereoselective manner. Thallium(III) is chemoselective in this rearrangement, reacting with the olefin without oxidation of the indole moiety. Other key transformations are the Bartoli's reaction to construct the heterocyclic ring and a Heck coupling to add the carbons atom that will originate the nonaromatic cycle.

引用

页码：5417 / 5420

页数：4

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