An asymmetric Maitland–Japp reaction: a highly enantioselective synthesis of tetrahydropyran-4-ones

A highly enantioselective synthesis of functionalized tetrahydropyran-4-ones has been achieved by the development of a catalytic asymmetric Maitland–Japp reaction using Chan’s diene as the nucleophile. This reaction has been used to synthesize the tetrahydropyran ring of (−)-centrolobine and the C9–C19 tetrahydropyran ring of (+)-phorboxazole B.