Stereocontrolled synthesis of quinine and quinidine
Stereocontrolled synthesis of quinine and quinidine
复制标题
DOI：
10.1016/j.tetlet.2004.03.085
复制
发表时间：
2004-05-03
影响因子：
1.8
通讯作者：
Kobayashi, Y
中科院分区：
文献类型：
--
作者：
Igarashi, J;Katsukawa, M;Kobayashi, Y
以单乙酸环戊烯为原料制备了二取代环戊烯，并通过氧化裂解烯烃部分转化为二取代哌啶，形成哌啶环。然后在侧链上与喹啉部分缩合，得到奎宁的烯烃前体。最后，烯烃通过相应的环氧化物转化为奎宁。奎尼丁是用类似的方法合成的。(C) 2004 Elsevier Ltd.版权所有。
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.