title: Construction of the benzylic quaternary carbon center of zoanthenol by intramolecular Mizoroki-Heck reaction of enone.
abstract: [reaction: see text]. Stereocontrolled synthesis of the ABC ring framework of zoanthenol has been achieved. Our studies show that a beta,beta-disubstituted enone can act as a good acceptor of arylpalladium intermediates in the formation of a congested benzylic quaternary carbon center through an intramoleculer Mizoroki-Heck reaction. The cis B/C ring system was stereoselectively converted to the trans-fused framework through a SmI2-promoted deoxygenation of the alpha-hydroxy ketone.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, and CREST, Japan Science and Technology Corporation (JST), Sendai 980-8578, Japan.
authors.forename: Go
authors.initials: G
authors.lastname: Hirai
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Koizumi
authors.forename: Sameh M
authors.initials: SM
authors.lastname: Moharram
authors.forename: Hiroki
authors.initials: H
authors.lastname: Oguri
authors.forename: Masahiro
authors.initials: M
authors.lastname: Hirama
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006572:Heterocyclic Compounds, Bridged-Ring / Q000737:chemistry*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001952:Bridged-Ring Compounds; D006572:Heterocyclic Compounds, Bridged-Ring; D007202:Indicators and Reagents; C457061:zoanthenol; D010165:Palladium