Organic & Biomolecular Chemistry 2013-09-21

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

Emerson Giovanelli, Lionel Moisan, Sébastien Comesse, Sébastien Leroux, Bernard Rousseau, Paul Hellier, Marc Nicolas, Eric Doris

Index: Org. Biomol. Chem. 11(35) , 5885-91, (2013)

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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.