Sequential One-Pot Cyclizations: Concise Access to the ABCE Tetracyclic Framework of Strychnos Alkaloids

被引：60

作者：

Sirasani, Gopal ^{[1
]}

Andrade, Rodrigo B. ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 10期

关键词：

OLEFIN CROSS-METATHESIS; BAYLIS-HILLMAN REACTION; STEREOSELECTIVE-SYNTHESIS; INDOLE ALKALOIDS; SYNTHETIC ENTRY; (+/-)-19,20-DIHYDROAKUAMMICINE; EFFICIENT; ECONOMY;

D O I：

10.1021/ol9004799

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sequential one-pot biscyclization route to the ABCE tetracyclic framework of Strychnos alkaloids has been developed. Specifically, the AgOTf-mediated spirocyclization of an appropriately functionalized indole 3-carbinamide afforded a stable spiroindolenine intermediate; subsequent addition of DBU to the reaction mixture effected an unprecedented intramolecular aza-Baylis-Hillman reaction, delivering a tetracyclic product in 70% isolated yield.

引用

页码：2085 / 2088

页数：4

共 37 条

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