Organic Letters
Organic Letters
5 years ago

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

Asymmetric Total Syntheses of Colchicine, β-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)
Xin Liu, Jing Zhao, Bo Chen, Xiao-Shui Peng, Long Min, Chuang-Chuang Li, Henry N. C. Wong, Shaoping Li, Ya-Jian Hu
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02224

DOI: 10.1021/acs.orglett.7b02224

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