title: Iron(III)/NaBH4-mediated additions to unactivated alkenes: synthesis of novel 20'-vinblastine analogues.
abstract: An Fe(III)/NaBH(4)-mediated reaction for the functionalization of unactivated alkenes is described defining the alkene substrate scope, establishing the exclusive Markovnikov addition, exploring a range of free radical traps, examining the Fe(III) salt and initiating hydride source, introducing H(2)O-cosolvent mixtures, and exploring catalytic variants. Its use led to the preparation of a novel, potent, and previously inaccessible C20'-vinblastine analogue.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Erick K
authors.initials: EK
authors.lastname: Leggans
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Barker
authors.forename: Katharine K
authors.initials: KK
authors.lastname: Duncan
authors.forename: Dale L
authors.initials: DL
authors.lastname: Boger
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001894:Borohydrides / Q000737:chemistry*; D002384:Catalysis; D005290:Ferric Compounds / Q000737:chemistry*; D015394:Molecular Structure; D014747:Vinblastine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D001894:Borohydrides; D005290:Ferric Compounds; D014747:Vinblastine; C025364:sodium borohydride