title: Novel skeleton transformation reaction of α-pyrone derivatives to spirobicyclo[3.1.0]hexane derivatives using dimethylsulfoxonium methylide.
abstract: By applying a skeleton transformation reaction using dimethylsulfoxonium methylide, a novel reaction was identified by which 5,6,7,8-tetrahydrocoumarin with the electron-withdrawing group at C3 was led to the spirobicyclo[3.1.0]hexane-cyclohexane derivative. Moreover, by establishing the scope of this reaction, it was confirmed that it is possible to apply this reaction to not only ring-fused α-pyrone derivatives but also alkyl-chain-substituted α-pyrone derivatives in moderate to good yields.
authors.affiliation: Kyoto Pharmaceutical University, 1 Misasagi-Shichono, Yamashina, Kyoto 607-8412, Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Miura
authors.forename: Navnath Dnyanoba
authors.initials: ND
authors.lastname: Yadav
authors.forename: Hiroki
authors.initials: H
authors.lastname: Iwasaki
authors.forename: Minoru
authors.initials: M
authors.lastname: Ozeki
authors.forename: Naoto
authors.initials: N
authors.lastname: Kojima
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yamashita
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D001643:Bridged Bicyclo Compounds; D006586:Hexanes; D011753:Pyrones; D013141:Spiro Compounds; D013452:Sulfonium Compounds; C554865:dimethylsulfoxonium methylide; C026385:n-hexane