Tetrahedron letters

Stereocontrolled synthesis of quinine and quinidine

…, M Katsukawa, YG Wang, HP Acharya, Y Kobayashi

文献索引：Igarashi, Junji; Katsukawa, Masahiro; Wang, Yong-Gang; Acharya, Hukum P.; Kobayashi, Yuichi Tetrahedron Letters, 2004 , vol. 45, # 19 p. 3783 - 3786

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被引用次数: 47

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.