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Enantioselective total synthesis of (−)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids

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Abstract

Here, 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.

Graphical abstract: Enantioselective total synthesis of (−)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids

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Publication details

The article was received on 25 Mar 2017, accepted on 30 Apr 2017 and first published on 05 May 2017


Article type: Edge Article
DOI: 10.1039/C7SC01341H
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Enantioselective total synthesis of (−)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids

    B. Chen, X. Liu, Y. Hu, D. Zhang, L. Deng, J. Lu, L. Min, W. Ye and C. Li, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC01341H

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