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

页码：6199 / 6207

页数：9

共 38 条

[1] Enantioselective total synthesis of (-)-alpha-kainic acid through free radical cyclization of an alkenyl monothioformimide [J].