title: 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.
authors.affiliation: CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette, France. eric.doris@cea.fr.
authors.forename: Emerson
authors.initials: E
authors.lastname: Giovanelli
authors.forename: Lionel
authors.initials: L
authors.lastname: Moisan
authors.forename: Sébastien
authors.initials: S
authors.lastname: Comesse
authors.forename: Sébastien
authors.initials: S
authors.lastname: Leroux
authors.forename: Bernard
authors.initials: B
authors.lastname: Rousseau
authors.forename: Paul
authors.initials: P
authors.lastname: Hellier
authors.forename: Marc
authors.initials: M
authors.lastname: Nicolas
authors.forename: Eric
authors.initials: E
authors.lastname: Doris
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics / Q000379:methods; D030008:Catharanthus / Q000737:chemistry*; D054879:Halogenation; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D014748:Vinca Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D014748:Vinca Alkaloids; C009667:vindoline; D014747:Vinblastine; C017836:catharanthine