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Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: Determination of the absolute configurations of the latter two alkaloids
Chen B.; Liu X.; Hu Y.-J.; Zhang D.-M.; Deng L.; Lu J.; Min L.; Ye W.-C.; Li C.-C.
2017
Source PublicationChemical Science
ISSN20416520
Volume8Issue:7Pages:4961
AbstractHere, we describe a concise, enantioselective, and scalable synthesis of (-)-colchicine (9.2% overall yield, >99% ee). Moreover, we have also achieved the first syntheses of (+)-demecolcinone and metacolchicine, and determined their absolute configurations. The challenging tricyclic 6-7-7 core of colchicinoids was efficiently introduced using an intramolecular oxidopyrylium-mediated [5 + 2] cycloaddition reaction. Notably, the synthesized colchicinoid 23 exhibited potent inhibitory activity toward the cell growth of human cancer cell lines (IC50 = ∼3.0 nM), and greater inhibitory activity towards microtubule assembly than colchicine, making it a promising lead in the search for novel anticancer agents. © 2017 The Royal Society of Chemistry.
DOI10.1039/c7sc01341h
URLView the original
Language英语
The Source to ArticleScopus
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Cited Times [WOS]:24   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionUniversity of Macau
Recommended Citation
GB/T 7714
Chen B.,Liu X.,Hu Y.-J.,et al. Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: Determination of the absolute configurations of the latter two alkaloids[J]. Chemical Science,2017,8(7):4961.
APA Chen B..,Liu X..,Hu Y.-J..,Zhang D.-M..,Deng L..,...&Li C.-C..(2017).Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: Determination of the absolute configurations of the latter two alkaloids.Chemical Science,8(7),4961.
MLA Chen B.,et al."Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: Determination of the absolute configurations of the latter two alkaloids".Chemical Science 8.7(2017):4961.
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