title: Total synthesis of (-)- and ent-(+)-vindoline.
abstract: [reaction: see text] Two exceptionally concise total syntheses of (-)- and ent-(+)-vindoline are detailed enlisting a diastereoselective tandem [4 + 2]/[3 + 2] cycloaddition of a 1,3,4-oxadiazole. The unique reaction cascade assembles the fully functionalized pentacyclic ring system of vindoline in a single step that forms four C-C bonds and three rings while introducing all requisite functionality and setting all six stereocenters within the central ring including three contiguous and four total quaternary centers.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Younggi
authors.initials: Y
authors.lastname: Choi
authors.forename: Hayato
authors.initials: H
authors.lastname: Ishikawa
authors.forename: Juraj
authors.initials: J
authors.lastname: Velcicky
authors.forename: Gregory I
authors.initials: GI
authors.lastname: Elliott
authors.forename: Michael M
authors.initials: MM
authors.lastname: Miller
authors.forename: Dale L
authors.initials: DL
authors.lastname: Boger
mesh_terms: D001688:Biological Products / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001688:Biological Products; C009667:vindoline; D014747:Vinblastine