Hydrogen-atom abstraction/cyclization in synthesis. Direct syntheses of coumestan and coumestrol

被引:61
|
作者
Kraus, GA [1 ]
Zhang, N
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
[2] Iowa State Univ, Toxicol Program, Ames, IA 50011 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 18期
关键词
D O I
10.1021/jo0004198
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of coumestrol has been achieved in five steps from 1,3-dimethoxybenzene. The key step is a photochemical cyclization of a glyoxylate ester.
引用
收藏
页码:5644 / 5646
页数:3
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