title: Reductive cleavage of tetrahydrofuryl sulfur-substituted oxiranes: application to the formal synthesis of Kumausyne and Kumausallene.
abstract: [reactions: see text] Readily available sulfinyl and sulfonyl tetrahydrofuran methanol derivatives have been transformed efficiently into a variety of substituted tetrahydrofuryl alcohols by treatment with (PhSe)2 in the presence of an excess of NaBH4. Alternatively, oxirane cleavage with MgI2 produces the related ketones, amenable to stereocontrolled reduction. This reductive cleavage methodology has been applied to short formal syntheses of trans-Kumausyne and Kumausallene.
authors.affiliation: Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain. iqofp19@iqog.csic.es
authors.forename: Roberto
authors.initials: R
authors.lastname: Fernández de la Pradilla
authors.forename: Carolina
authors.initials: C
authors.lastname: Alhambra
authors.forename: Alejandro
authors.initials: A
authors.lastname: Castellanos
authors.forename: Jorge
authors.initials: J
authors.lastname: Fernández
authors.forename: Pilar
authors.initials: P
authors.lastname: Manzano
authors.forename: Carlos
authors.initials: C
authors.lastname: Montero
authors.forename: Mercedes
authors.initials: M
authors.lastname: Ureña
authors.forename: Alma
authors.initials: A
authors.lastname: Viso