Stereoselective Total Synthesis of (3R,5R)-5-Hydroxy-de-O-methyllasiodiplodin via the Prins Cyclization

A practical stereoselective total synthesis of (3R,5R)-5-hydroxy-de-O-methyllasiodiplodin has been accomplished via Prins cyclization. It exhibits potato microtuber inducing activity. The synthetic sequence involves Prins cyclization, reductive opening of the pyran ring, esterification, and ring-closing metathesis (RCM) as the key steps.