Allergenic α-Methylene-γ-butyrolactones. β-Hydroxy-α-methylene-γ-butyrolactones. 2. Syntheses from Ethyl 2-(Phenylthio)propionate and α-Acetoxy Aldehydes

Article abstract of DOI:10.1021/jo00164a014

β-Hydroxy-and β-acetoxy-α-methylene-γ-butyrolactones were prepared from α-acetoxy aldehydes and ethyl 2-(phenylthio)propionate.Diastereomeric sulfides 8-11 were separated, oxidized, and thermally eliminated, leading to β-acetoxy-exo-methylene lactones 23-25 and to butenolides 26-28, depending on the configuration of the phenylsulfinyl group. β-Hydroxy lactones 19 were prepared by saponification of the β-acetoxy derivatives.