A mild new procedure for production, cyclization and trapping of amidyl radicals: application to a formal total synthesis of peduncularine

被引：49

作者：

Lin, XC ^{[1
]}

Stien, D ^{[1
]}

Weinreb, SM ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 14期

基金：

美国国家卫生研究院;

关键词：

cyclization; radicals and radical reactions; nitrogen heterocycles; hydroxamic acids and derivatives; alkaloids;

D O I：

10.1016/S0040-4039(00)00194-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of an olefinic hydroxamic acid with tert-butylsulfinyl chloride and Hunig's base from -50 degrees C to room temperature in the presence of a radical trap such as diphenyl diselenide, diphenyl disulfide or TEMPO affords a functionalized product derived from an amidyl radical cyclization. The methodology has been used in a formal total synthesis of the 6-azabicyclo[3.2.1] octane-containing indole alkaloid peduncularine. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2333 / 2337

页数：5

共 21 条

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