Stereocontrolled synthesis of quinine and quinidine

被引：63

作者：

Igarashi, J ^{[1
]}

Katsukawa, M ^{[1
]}

Wang, YG ^{[1
]}

Acharya, HP ^{[1
]}

Kobayashi, Y ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 19期

关键词：

quinine; quinidine; piperidine; cyclopentene-1,3-diol monoacetate; epoxide ring opening;

D O I：

10.1016/j.tetlet.2004.03.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Disubstituted cyclopentene was prepared from cyclopentene monoacetate and transferred into disubstituted piperidine via oxidative cleavage of the olefin moiety followed by piperidine ring formation. The piperidine was then condensed at the side chain with a quinoline part to afford the olefin precursor of quinine. Finally, the olefin was converted into quinine through the corresponding epoxide. Quinidine was synthesized in a similar way. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3783 / 3786

页数：4

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