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Issue 35, 2013
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Synthesis of fluorinated catharanthine analogues and investigation of their biomimetic coupling with vindoline

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Abstract

The syntheses of 20,20-difluorocatharanthine and congeners, starting from the naturally occurring catharanthine, are reported. The fluorinated catharanthine analogues were investigated as potential precursors to dimeric Vinca alkaloids of the vinflunine family. However, the biomimetic coupling of the fluorinated catharanthine derivatives with vindoline led to unexpected alkaloid structures, the formation of which was rationalized.

Graphical abstract: Synthesis of fluorinated catharanthine analogues and investigation of their biomimetic coupling with vindoline

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Publication details

The article was received on 06 Jun 2013, accepted on 18 Jul 2013 and first published on 18 Jul 2013


Article type: Paper
DOI: 10.1039/C3OB41170B
Org. Biomol. Chem., 2013,11, 5885-5891

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    Synthesis of fluorinated catharanthine analogues and investigation of their biomimetic coupling with vindoline

    E. Giovanelli, L. Moisan, S. Comesse, S. Leroux, B. Rousseau, P. Hellier, M. Nicolas and E. Doris, Org. Biomol. Chem., 2013, 11, 5885
    DOI: 10.1039/C3OB41170B

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