A Sequential Acyl Thiol-Ene and Thiolactonization Approach for the Synthesis of δ-Thiolactones

A novel strategy for the synthesis of delta-thiolactones from inexpensive and readily available gamma-unsaturated esters has been developed. This strategy incorporates a radical acyl thiol-ene reaction as the key C-S bond forming step. Cyclization is achieved via a Steglich-type thiolactonization of 5-mercaptopentanoic acids. We report the facile and scalable synthesis of delta-thiolactones in moderate to good yield under mild reaction conditions with tolerance for a range of functional groups.