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Asymmetric Total Syntheses of Colchicine, beta-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME)
Liu, Xin; Hu, Ya-Jian; Chen, Bo; Min, Long; Peng, Xiao-Shui; Zhao, Jing; Li, Shaoping; Wong, Henry N. C.; Li, Chuang-Chuang
2017-09
Source PublicationORGANIC LETTERS
ISSN1523-7060
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 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.
DOI10.1021/acs.orglett.7b02224
URLView the original
Indexed BySCI ; CCR
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000409566400051
PublisherAMER CHEMICAL SOC
The Source to ArticleWOS
Fulltext Access
Citation statistics
Cited Times [WOS]:1   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionUniversity of Macau
Recommended Citation
GB/T 7714
Liu, Xin,Hu, Ya-Jian,Chen, Bo,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 Liu, Xin.,Hu, Ya-Jian.,Chen, Bo.,Min, Long.,Peng, Xiao-Shui.,...&Li, Chuang-Chuang.(2017).Asymmetric Total Syntheses of Colchicine, beta-Lumicolchicine, and Allocolchicinoid N-Acetylcolchinol-O-methyl Ether (NCME).ORGANIC LETTERS,19(17),4612-4615.
MLA Liu, Xin,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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