Stereoselective synthesis of (10S, 12S)-10-hydroxy-12-methyl-1-oxacyclododecane-2, 5-dione via Prins cyclization

The total synthesis of (10S,12S)-10-hydroxy-12-methyl-1-oxacyclododecane-2,5-dione is described proving the versatility of the Prins cyclization in natural products synthesis. The approach is convergent and highly stereoselective. Prins cyclization, esterification, ring-closing metathesis and oxidation reactions are utilized as key steps in the synthesis of this macrolactone