title: A non-iterative, flexible, and highly stereoselective synthesis of polydeoxypropionates--synthesis of (+)-vittatalactone.
abstract: A short sequence comprising an oxy-Cope rearrangement, iridium-catalyzed hydrogenation, and enolate methylation provides trideoxypropionates with excellent diastereocontrol. A straightforward synthesis of the cucumber beetle pheromone (+)-vittatalactone illustrates this new strategy.
authors.affiliation: Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Christian F
authors.initials: CF
authors.lastname: Weise
authors.forename: Matthias
authors.initials: M
authors.lastname: Pischl
authors.forename: Andreas
authors.initials: A
authors.lastname: Pfaltz
authors.forename: Christoph
authors.initials: C
authors.lastname: Schneider
mesh_terms: D000818:Animals; D002384:Catalysis; D001517:Coleoptera / Q000737:chemistry; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010675:Pheromones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D010675:Pheromones; C497413:vittatalactone; D007495:Iridium