title: Stereoselective construction of tetra-substituted tetrahydrofuran compounds from benzylic hemiacetal in the presence of H2 and a Pd catalyst: stereoselective synthesis of a stereoisomer of (-)-virgatusin and its antimicrobiological activity.
abstract: Tetra-substituted tetrahydrofuran compounds were stereoselectively prepared from benzylic hemiacetal in the neutral condition by employing the simple reagent, H(2), and a Pd catalyst. The stereoselective conversion of benzylic hemiacetal to two different stereoisomers of the tetrasubstituted tetrahydrofuran compound was observed. One of these tetrahydrofuran compounds was converted to the virgatusin stereoisomer to estimate its antimicrobiological activity.
authors.affiliation: Faculty of Agriculture, Ehime University, Matsuyama, Ehime, Japan.
authors.forename: Tomofumi
authors.initials: T
authors.lastname: Nakato
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Tago
authors.forename: Koichi
authors.initials: K
authors.lastname: Akiyama
authors.forename: Masafumi
authors.initials: M
authors.lastname: Maruyama
authors.forename: Takuya
authors.initials: T
authors.lastname: Sugahara
authors.forename: Taro
authors.initials: T
authors.lastname: Kishida
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001593:Benzyl Compounds; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009904:Optical Rotation; D011108:Polymers / Q000737:chemistry; D012997:Solvents
chemical_list: D000900:Anti-Bacterial Agents; D001593:Benzyl Compounds; D005663:Furans; D011108:Polymers; D012997:Solvents; C018801:acetal copolymer; C511226:virgatusin; C018674:tetrahydrofuran