The odd couple: The synthesis of 20,20-difluorocatharanthine starting from naturally occurring catharanthine is reported. The fluorinated catharanthine analogue was investigated as a potential precursor to dimeric Vinca alkaloids of the vinflunine family. However, the biomimetic coupling of difluorocatharanthine with vindoline led to unexpected products, the formation of which was rationalized (see scheme).
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