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
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
收藏
页码:2333 / 2337
页数:5
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