Total Syntheses of Bisdehydroneostemoninine and Bisdehydrostemoninine by Catalytic Carbonylative Spirolactonization

被引：71

作者：

Ma, Kaiqing ^{[1
,2
,3
]}

Yin, Xianglin ^{[1
,2
]}

Dai, Mingji ^{[1
,2
]}

机构：

[1] Purdue Univ, Ctr Canc Res, Dept Chem, W Lafayette, IN 47907 USA

[2] Purdue Univ, Inst Drug Discovery, W Lafayette, IN 47907 USA

[3] Shanxi Univ, Modern Res Ctr Tradit Chinese Med, Taiyuan 03006, Shanxi, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 46期

关键词：

alkaloids; cyclizations; natural products; palladium; total synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; STEMONA; ALKALOIDS; ROOTS; ALCOHOLS; CHEMISTRY; LACTONES; ALLYL;

D O I：

10.1002/anie.201809114

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total syntheses of the stemona alkaloids bisdehydroneostemoninine and bisdehydrostemoninine in racemic forms have been achieved. The synthetic strategy features a novel palladium-catalyzed carbonylative spirolactonization of a hydroxycyclopropanol to rapidly construct the oxaspirolactone moiety. It also features a Lewis acid promoted tandem Friedel-Crafts cyclization and lactonization to form the 5-7-5 tricyclic core of the target stemona alkaloids.

引用

页码：15209 / 15212

页数：4

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