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Asymmetric Total Syntheses of Colchicine, β-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)
Liu X.2; Hu Y.-J.2; Chen B.3; Min L.3; Peng X.-S.1; Zhao J.2; Li S.2; Wong H.N.C.1; Li C.-C.3
2017-09-01
Source PublicationOrganic Letters
ISSN15237052 15237060
Volume19Issue:17Pages:4612-4615
AbstractA 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.
DOI10.1021/acs.orglett.7b02224
URLView the original
Language英語
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Cited Times [WOS]:3   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionUniversity of Macau
Affiliation1.Chinese University of Hong Kong
2.Universidade de Macau
3.Southern University of Science and Technology
Recommended Citation
GB/T 7714
Liu X.,Hu Y.-J.,Chen B.,et al. Asymmetric Total Syntheses of Colchicine, β-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)[J]. Organic Letters,2017,19(17):4612-4615.
APA Liu X..,Hu Y.-J..,Chen B..,Min L..,Peng X.-S..,...&Li C.-C..(2017).Asymmetric Total Syntheses of Colchicine, β-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME).Organic Letters,19(17),4612-4615.
MLA Liu X.,et al."Asymmetric Total Syntheses of Colchicine, β-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)".Organic Letters 19.17(2017):4612-4615.
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