title: A general, asymmetric, and noniterative synthesis of trideoxypropionates. Straightforward syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone.
abstract: A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement, an iridium-catalyzed hydrogenation, and an auxiliary-controlled enolate methylation, trideoxypropionates with easily adjustable relative configuration were synthesized in excellent yields. In addition, the functionalized end groups allow for chemoselective manipulations and further elongation of the chain. The underlying strategy constitutes the first noniterative process for the assembly of polydeoxypropionates and has further been applied in total syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone, which had been isolated from the striped cucumber beetle Acalymma vittatum.
authors.affiliation: Institut für Organische Chemie, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
authors.forename: Christian F
authors.initials: CF
authors.lastname: Weise
authors.forename: Matthias C
authors.initials: MC
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; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D007783:Lactones / Q000138:chemical synthesis*; D010675:Pheromones / Q000138:chemical synthesis*; D011422:Propionates / Q000138:chemical synthesis*
chemical_list: D007783:Lactones; D010675:Pheromones; D011422:Propionates; C497413:vittatalactone