The Journal of Organic Chemistry

Allergenic. alpha.-methylene-. gamma.-butyrolactones.. beta.-Hydroxy-. alpha.-methylene-. gamma.-butyrolactones. 2. Syntheses from ethyl 2-(phenylthio) propionate …

P Barbier, C Benezra

Index: Barbier, Pierre; Benezra, Claude Journal of Organic Chemistry, 1983 , vol. 48, # 16 p. 2705 - 2709

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Citation Number: 40

Abstract

@-Hydroxy-and@-acetoxy-a-methylene-y-butyrolactones were prepared from a-acetoxy aldehydes and ethyl 2-(pheny1thio) propionate. Diastereomeric sulfides 8-1 1 were separated, oxidized, and thermally eliminated, leading to@-acetoxy-exo-methylene lactones 23-25 and to butenolides 26-28, depending on the configuration of the phenylsulfinyl group.@-Hydroxy lactones 19 were prepared by saponification of the@-acetoxy ...

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