Total Synthesis of (+)‐Dactylolide through an Efficient Sequential Peterson Olefination and Prins Cyclization Reaction

Abstract

Key steps in the total synthesis of the macrolide natural product (+)-dactylolide (see formula) include two enantioselective vinylogous Mukaiyama reactions, fragment coupling through acetal formation, a sequential Peterson olefination/Prins cyclization reaction that proceeds under very mild conditions, and a Mislow–Evans rearrangement to effect the transposition of an allylic alcohol.