A General Synthesis of (±)-γ-Substituted γ-Butyrolactones Using a Kinetic Alkylation-Ozonolysis Procedure

Abstract

A synthesis of (±)-γ-substituted γ-butyrolactones is described in which the key intermediates, γ-ketoesters, are prepared from the readily available 6-methyl-5-hepten-2-one using a kinetic alkylation-ozonolysis procedure; the method allows terminal ester and Z-alkene groups to be incorporated into the side-chain and thus can be used for the synthesis of (±)-γ-jasmolactone as well as other naturally occurring lactones.