A general strategy for the synthesis of indoloquinolizine alkaloids via a cyanide-catalyzed imino-Stetter reaction

被引：17

作者：

Park, Eunjoon ^{[1
]}

Cheon, Cheol-Hong ^{[1
]}

机构：

[1] Korea Univ, Dept Chem, 145 Anam Ro, Seoul 02841, South Korea

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 48期

基金：

新加坡国家研究基金会;

关键词：

HIGHLY STEREOSELECTIVE-SYNTHESIS; ZWITTERIONIC INDOLE ALKALOIDS; DIRECTED METALATION ROUTE; NATURAL-PRODUCT SYNTHESIS; RING-SYSTEM; DERIVATIVES; CYCLIZATION; PYRIDINES; (+/-)-TANGUTORINE; FLAVOPEREIRINE;

D O I：

10.1039/c7ob02691a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.

引用

页码：10265 / 10275

页数：11

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