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

被引：18

作者：

Liu, Xin ^{[1
,2
]}

Hu, Ya-Jian ^{[1
,2
]}

Chen, Bo ^{[2
]}

Min, Long ^{[2
]}

Peng, Xiao-Shui ^{[3
]}

Zhao, Jing ^{[1
]}

Li, Shaoping ^{[1
]}

Wong, Henry N. C. ^{[3
]}

Li, Chuang-Chuang ^{[2
]}

机构：

[1] Univ Macau, Inst Chinese Med Sci, Macau, Peoples R China

[2] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China

[3] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 17期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; 5+2 CYCLOADDITION REACTIONS; CARBON-CARBON BONDS; CONJUGATED YNONES; ANTITUMOR AGENTS; ARYL KETONES; RING; DECARBONYLATION; OXIDATION; TUBULIN;

D O I：

10.1021/acs.orglett.7b02224

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 beta-lumicolchicine and N-acetylcolchinol-O-methyl ether (NCME) were achieved. Notably, NCME was synthesized from beta-lumicolchicine by an unusual decarbonylation and electrocyclic ring-opening cascade reaction.

引用

页码：4612 / 4615

页数：4

共 14 条

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[10] Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin
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