Radical cyclization in heterocycle synthesis. Part 10: A concise synthesis of (-)-kainic acid via sulfanyl radical addition-cyclization-elimination reaction

被引：78
|
作者：
Miyata, O [1 ]
Ozawa, Y [1 ]
Ninomiya, I [1 ]
Naito, T [1 ]
机构：
[1] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan
来源：
TETRAHEDRON | 2000年 / 56卷 / 34期
关键词：
kainic acid; thiophenol; radical cyclization; pyrrolidine;
D O I：
10.1016/S0040-4020(00)00579-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sulfanyl radical addition-cyclization-elimination of diallylamines in the presence of thiophenol and AIBN gave the 2,3,4-trisubstituted pyrrolidine in high yield. This reaction was extended to a radical cyclization using a catalytic amount of thiophenol. A successful application was demonstrated by the asymmetric synthesis of (-)-kainic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：6199 / 6207
页数：9
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