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

Xin Liu | Zendy; YaJian Hu | Zendy; Bo Chen | Zendy; Long Min | Zendy; XiaoShui Peng | Zendy; Jing Zhao | Zendy; Shaoping Li | Zendy; Henry Ν. C. Wong | Zendy; ChuangChuang Li | Zendy

Open Access

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

Author(s) -

Xin Liu,

YaJian Hu,

Bo Chen,

Long Min,

XiaoShui Peng,

Jing Zhao,

Shaoping Li,

Henry Ν. C. Wong,

ChuangChuang Li

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b02224

Subject(s) - chemistry , enantioselective synthesis , tropolone , ring (chemistry) , decarbonylation , ether , regioselectivity , yield (engineering) , total synthesis , colchicine , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy , medicine

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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