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Issue 8, 2016
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Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums

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Abstract

An efficient and novel strategy for the enantioselective syntheses of various iboga alkaloids has been developed. The salient features include a gold-catalyzed oxidation of a terminal alkyne followed by cyclization, a Stevens rearrangement and a tandem sequence that combines the gold-catalyzed oxidation, cyclization and [1,2]-shift. The catharanthine analogs provided by our approach were further converted to the vinca alkaloid vinblastine and its analogs, which confirmed the remarkable sensitivity of the cytotoxicity to the C20′ substituent of vinblastine.

Graphical abstract: Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums

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Publication details

The article was received on 29 Feb 2016, accepted on 13 May 2016 and first published on 16 May 2016


Article type: Edge Article
DOI: 10.1039/C6SC00932H
Citation: Chem. Sci., 2016,7, 5530-5536
  • Open access: Creative Commons BY license
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    Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums

    Y. Zhang, Y. Xue, G. Li, H. Yuan and T. Luo, Chem. Sci., 2016, 7, 5530
    DOI: 10.1039/C6SC00932H

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