Studies on sesquiterpenoids. Part XVI. A new synthetic method for α-methylene-γ-lactones; total synthesis of (±)-isoalantolactone

Abstract

α-Methylene-γ-lactones have been synthesised from α-formyl-γ-lactones by way of α-hydroxymethyl-γ-lactones. This method is very simple and efficient for syntheses of high-molecular-weight compounds with this functional group. The method was applied to the synthesis of (±)-isoalantolactone (8aβ-methyl-3,5-dimethylene-3aα,4aα,9aα-perhydronaphtho[2,3-b]furan-2-one).