γ-selective hydroxylation of α,β,γ,δ-unsaturated carbonyl compounds and its application to syntheses of (±)-6-hydroxyshogaol and related furanoids

Article abstract of DOI:10.1016/0040-4039(95)00173-A

α,β,γ,δ-Unsaturated carbonyl compounds were converted regioselectively into γ-hydroxy-α,β-unsaturated carbonyl compounds by reduction-oxygenation with molecular oxygen and triethylsilane in the presence of cobalt(II) porphyrin as a catalyst followed by treatment with trimethyl phosphite. (±)-Hydroxyshogaol and related furanoids isolated from ginger were synthesized via this method.