Formal synthesis of (-)-aphanorphine using seqnential photomediated radical reactions of dithiocarbamates

被引：79

作者：

Grainger, Richard S. ^{[1
]}

Welsh, Emma J. ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 28期

基金：

英国工程与自然科学研究理事会;

关键词：

cyclization; metathesis; oxidation; radical reactions; sulfinamides;

D O I：

10.1002/anie.200701055

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Time to change the light bulb: An alkyl dithiocarbamate, itself formed through a photoinitiated group-transfer cyclization of a carbamoyl radical, undergoes a second photomediated radical process initiated with a different light source. These two reactions, which proceed through the same cyclohexenyl radical intermediate, are key steps in a new asymmetric synthesis of the alkaloid aphanorphine. TEMPO = 2,2,6,6-tetramethyl-1-piperidinoxyl radical. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5377 / 5380

页数：4

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