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Asymmetric Total Syntheses of Colchicine, beta-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)
Xin Liu1,2; Ya-Jian Hu1,2; Bo Chen2; Long Min2; Xiao-Shui Peng3; Jing Zhao1; Shaoping Li1; Henry N. C. Wong3; Chuang-Chuang Li2
2017-08-19
Source PublicationORGANIC LETTERS
ISSN1523-7060
Volume19Issue:17Pages:4612-4615
Abstract

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.

KeywordEnantioselective Total-synthesis 5+2 Cycloaddition Reactions Carbon-carbon Bonds Conjugated Ynones Antitumor Agents Aryl Ketones Ring Decarbonylation Oxidation Tubulin
DOIhttp://dx.doi.org/10.1021/acs.orglett.7b02224
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000409566400051
PublisherAMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
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Cited Times [WOS]:8   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Corresponding AuthorJing Zhao; Shaoping Li; Chuang-Chuang Li
Affiliation1.Institute of Chinese Medical Sciences, University of Macau, Macao, China
2.Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
3.Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China
First Author AffilicationInstitute of Chinese Medical Sciences
Corresponding Author AffilicationInstitute of Chinese Medical Sciences
Recommended Citation
GB/T 7714
Xin Liu,Ya-Jian Hu,Bo Chen,et al. Asymmetric Total Syntheses of Colchicine, beta-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)[J]. ORGANIC LETTERS,2017,19(17):4612-4615.
APA Xin Liu.,Ya-Jian Hu.,Bo Chen.,Long Min.,Xiao-Shui Peng.,...&Chuang-Chuang Li.(2017).Asymmetric Total Syntheses of Colchicine, beta-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME).ORGANIC LETTERS,19(17),4612-4615.
MLA Xin Liu,et al."Asymmetric Total Syntheses of Colchicine, beta-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)".ORGANIC LETTERS 19.17(2017):4612-4615.
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