A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents

被引：111

作者：

Theeraladanon, C ^{[1
]}

Arisawa, M ^{[1
]}

Nishida, A ^{[1
]}

Nakagawa, M ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 13期

关键词：

quinine; chloroquine; quinoline alkaloid; anti-malaria; ring-closing metathesis (RCM); silylenol-ether;

D O I：

10.1016/j.tet.2004.01.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2-dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3017 / 3035

页数：19

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