UM
Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids
Chen, Bo; Liu, Xin; Hu, Ya-Jian; Zhang, Dong-Mei; Deng, Lijuan; Lu, Jieyu; Min, Long; Ye, Wen-Cai; Li, Chuang-Chuang
2017-07
Source PublicationCHEMICAL SCIENCE
ISSN2041-6520
Volume8Issue:7Pages:4961-4966
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 = similar to 3.0 nM), and greater inhibitory activity towards microtubule assembly than colchicine, making it a promising lead in the search for novel anticancer agents.
DOI10.1039/c7sc01341h
URLView the original
Indexed BySCI ; IC ; CCR
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000404617300029
PublisherROYAL SOC CHEMISTRY
The Source to ArticleWOS
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Citation statistics
Cited Times [WOS]:24   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionUniversity of Macau
Recommended Citation
GB/T 7714
Chen, Bo,Liu, Xin,Hu, Ya-Jian,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):4961-4966.
APA Chen, Bo.,Liu, Xin.,Hu, Ya-Jian.,Zhang, Dong-Mei.,Deng, Lijuan.,...&Li, Chuang-Chuang.(2017).Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids.CHEMICAL SCIENCE,8(7),4961-4966.
MLA Chen, Bo,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):4961-4966.
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