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Gelsemine support studies: Observation of an unusual free radical cyclization-fragmentation sequence

被引：4
作者：
Hart, DJ
Kuzmich, D
机构：
[1] Department of Chemistry, Ohio State University, Columbus, Ohio, 43210
来源：
JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 1995年 / 42卷 / 06期
关键词：
radical cyclization; radical fragmentation; oxindole; tri-n-butyltin hydride; tris(trimethylsilyl)silane; (+/-)-gelsemine; (+/-)-oxogelsemine;
D O I：
10.1002/jccs.199500118
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Treatment of vinylogous urethanes 9a and 9b with tri-n-butyltin hydride generated a free radical that underwent cyclization-fragmentation to afford oxindole-ketones 10 and 11 in high yield. Vinylogous methane 13, gave only cyclization-reduction products 15 and 16 upon treatment with tri-n-butyltin hydride at 80 degrees C, but also afforded a low yield of cyclization-fragmentation product 14 upon treatment with tris(trimethylsilyl)silane at 140 degrees C.
引用
收藏
页码：873 / 875
页数：3
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