Enantioselective total synthesis of (+)-homochelidonine by a PdII-catalyzed asymmetric ring-opening reaction of a meso-azabicyclic alkene with an aryl boronic acid

被引：73

作者：

McManus, Helen A. ^{[1
]}

Fleming, Matthew J. ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Chem Labs, Toronto, ON M5S 3H6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 03期

关键词：

alkaloids; asymmetric catalysis; polycycles; ring-opening reactions; total synthesis;

D O I：

10.1002/anie.200603945

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) An efficient and highly convergent enantioselective synthesis of (+)-homochelidonine has been achieved (see scheme; Cbz = benzyloxycarbonyl, MOM = methoxymethyl) and relied on a new and powerful desymmetrizing ring-opening reaction of a meso-azabicycle with an aryl boronic acid. The route should allow access to other hexahydrobenzo[c]phenanthridine alkaloids. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：433 / 436

页数：4

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