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Synthesis of Difluorocatharanthine and Investigation of its Biomimetic Coupling with Vindoline

Authors

  • Dr. Emerson Giovanelli,

    1. CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette (France), Fax: (+33) 169-08-79-91
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  • Dr. Lionel Moisan,

    1. CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette (France), Fax: (+33) 169-08-79-91
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  • Dr. Sébastien Leroux,

    1. CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette (France), Fax: (+33) 169-08-79-91
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  • Dr. Sébastien Comesse,

    1. CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette (France), Fax: (+33) 169-08-79-91
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  • Dr. Bernard Rousseau,

    1. CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette (France), Fax: (+33) 169-08-79-91
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  • Dr. Paul Hellier,

    1. Les Laboratoires Pierre Fabre, Centre de Développement de Chimie Industrielle, 16 rue Jean Rostand, 81600 Gaillac (France)
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  • Dr. Marc Nicolas,

    1. Les Laboratoires Pierre Fabre, Centre de Développement de Chimie Industrielle, 16 rue Jean Rostand, 81600 Gaillac (France)
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  • Dr. Eric Doris

    Corresponding author
    1. CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette (France), Fax: (+33) 169-08-79-91
    • CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette (France), Fax: (+33) 169-08-79-91
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Abstract

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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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