title: Synthesis of (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine enabled by photoredox catalysis in flow.
abstract: Natural product modification with photoredox catalysis allows for mild, chemoselective access to a wide array of related structures in complex areas of chemical space, providing the possibility for novel structural motifs as well as useful quantities of less abundant congeners. While amine additives have been used extensively as stoichiometric electron donors for photocatalysis, the controlled modification of amine substrates through single-electron oxidation is ideal for the synthesis and modification of alkaloids. Here, we report the conversion of the amine (+)-catharanthine into the natural products (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine utilizing visible light photoredox catalysis.
authors.affiliation: Department of Chemistry, University of Michigan , Ann Arbor, Michigan 48109, United States.
authors.forename: Joel W
authors.initials: JW
authors.lastname: Beatty
authors.forename: Corey R J
authors.initials: CR
authors.lastname: Stephenson
mesh_terms: D002384:Catalysis; D007050:Ibogaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008027:Light; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D013237:Stereoisomerism; D014748:Vinca Alkaloids / Q000737:chemistry
chemical_list: D026121:Indole Alkaloids; D014748:Vinca Alkaloids; C553348:pseudotabersonine; D007050:Ibogaine; C011734:coronardine; C017836:catharanthine