title: Asymmetric synthesis of the tetrahydropyran ring, C32-C38 fragment, of phorboxazoles.
abstract: The asymmetric synthesis of a model aldehyde (2R,6R)-2 and the C32-C38 fragment of phorboxazoles, (2R,4R,6R)-1, is described using a sulfoxide as chiral auxiliary. Key advances include the stereoselective reductions of beta-keto- or beta,gamma-diketosulfoxides, the acid-catalyzed cyclization of enantiopure sulfinyl hydroxy ketone precursors to the tetrahydropyran ring, and the Pummerer reaction on the pendant sulfoxide to create the formyl group.
authors.affiliation: Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain.
authors.forename: Yasmin
authors.initials: Y
authors.lastname: Brinkmann
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Carreño
authors.forename: Antonio
authors.initials: A
authors.lastname: Urbano
authors.forename: Françoise
authors.initials: F
authors.lastname: Colobert
authors.forename: Guy
authors.initials: G
authors.lastname: Solladié