Issue 35, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
06 Jun 2013
Accepted
18 Jul 2013
First published
18 Jul 2013

Org. Biomol. Chem., 2013,11, 5885-5891

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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