Ierasia Triandafillidi

An Efficient Synthesis of γ-Lactones Utilizing Ketoacids and Trimethylsulfoxonium Iodide

γ-Lactones are very important moieties in natural products, products of biological importance, perfumes and food additives. Thus, many synthetic approaches for the synthesis of lactones have been devised, utilizing as starting materials a variety of organic compounds. Herein, our laboratory contributes in the synthesis of lactones via alternative and complementary methodologies.

The Corey-Chaykovsky epoxidation is one of the oldest methods for the synthesis of terminal epoxides from carbonyl compounds. Herein, we present a simplified extension of the Corey-Chaykovsky epoxidation, where ketoacids are employed as the substrates and commercially available trimethylsulfoxonium iodide as the carbon-atom homologating reagent. Initially, the epoxidation event is taking place, followed by a cyclization. Lactones are produced in a single step in satisfactory to excellent yields.