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Asymmetric Total Syntheses of Colchicine, β‑Lumicolchicine, and Allocolchicinoid N‑Acetylcolchinol‑O‑methyl Ether (NCME)

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posted on 2017-08-19, 00:00 authored by Xin Liu, Ya-Jian Hu, Bo Chen, Long Min, Xiao-Shui Peng, Jing Zhao, Shaoping Li, Henry N. C. Wong, Chuang-Chuang Li
A concise and highly enantioselective synthesis of colchicine (>99% ee) in eight steps and 9.3% overall yield, without the need for protecting groups, was developed. A unique Wacker oxidation was used for enabling regioselective construction of the highly oxidized and synthetic challenging tropolone C-ring. Furthermore, asymmetric syntheses of β-lumicolchicine and N-acetylcolchinol-O-methyl ether (NCME) were achieved. Notably, NCME was synthesized from β-lumicolchicine by an unusual decarbonylation and electrocyclic ring-opening cascade reaction.

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