title: Synthesis of C-15 vindoline analogues by palladium-catalyzed cross-coupling reactions.
abstract: Described are general protocols for the rapid construction of various C-15-substituted analogues of vindoline using palladium-catalyzed cross-coupling reactions. The required bromo- and iodovindolines were prepared in high yield by the reaction of vindoline with N-bromosuccinimide or N-iodosuccinimide, respectively. The study not only led to the preparation of a number of structurally novel vindoline analogues but also opens the door to new strategies for the synthesis of vinblastine, vincristine, and related anticancer agents. Also described is the conversion of ent-tabersonine to ent-vindoline.
authors.affiliation: Department of Chemistry, University of Chicago, Chicago, Illinois 60637, USA.
authors.forename: Peter D
authors.initials: PD
authors.lastname: Johnson
authors.forename: Jeong-Hun
authors.initials: JH
authors.lastname: Sohn
authors.forename: Viresh H
authors.initials: VH
authors.lastname: Rawal
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002384:Catalysis; D026121:Indole Alkaloids / Q000737:chemistry; D008722:Methods; D010165:Palladium / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D000970:Antineoplastic Agents; D026121:Indole Alkaloids; D011804:Quinolines; D013388:Succinimides; C009373:tabersonine; C009667:vindoline; D010165:Palladium; D014747:Vinblastine