A Concise Palladium-Catalyzed Carboamination Route to (±)-Tylophorine

被引：33

作者：

Rossiter, Lana M. ^{[1
]}

Slater, Meagan L. ^{[1
]}

Giessert, Rachel E. ^{[1
]}

Sakwa, Samuel A. ^{[1
]}

Herr, R. Jason ^{[1
]}

机构：

[1] AMRI, Dept Med Chem, Albany, NY 12212 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 24期

关键词：

PHENANTHROINDOLIZIDINE ALKALOIDS; STEREOSELECTIVE-SYNTHESIS; TYLOPHORA ALKALOIDS; MILD CONDITIONS; ALKENES; ANALOGS; PYRROLIDINES; CARBOETHERIFICATION; CRYPTOPLEURINE; CHLORIDE;

D O I：

10.1021/jo902114u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the racemic natural product tylophorine [(+/-)-1] has been demonstrated using the palladium-catalyzed carboamination method developed by Wolfe and coworkers. In this case, an electron-rich aryl bromide 18 was prepared in four steps and subjected to palladium-catalyzed Wolfe carboamination conditions with olefinic carbamate 7 to provide the racemic 2-(arylmethyl)pyrrolidine (+/-)-19 in good yield and was further elaborated to racemic tylophorine. This application of the Wolfe carboamination protocol as a key step to construct a natural product provides further evidence of the utility of the method.

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收藏

页码：9554 / 9557

页数：4

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