title: Oxidative ipso-rearrangement performed by a hypervalent iodine reagent and its application.
abstract: An oxidative ipso-rearrangement mediated by a hypervalent iodine reagent that enables rapid generation of a functionalized dienone system containing a quaternary carbon center connected to several sp(2) centers has been developed. The process occurs through transfer of an aryl group from a silyl segment present on the lateral chain. As an illustration of the potential of this transformation, a total synthesis of sceletenone, a small alkaloid, is described.
authors.affiliation: Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8 Québec, Canada.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Jacquemot
authors.forename: Sylvain
authors.initials: S
authors.lastname: Canesi
mesh_terms: D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*
chemical_list: D006574:Heterocyclic Compounds, 2-Ring; D012821:Silanes; C577171:sceletenone; D007455:Iodine