An alternative stereoselective synthesis of (-)-1-tetrahydropyrenophorol

Abstract

Macrodiolides have become highly attractive target molecules because of their interesting structural features and biological properties, including antibacterial, antifungal, cytotoxic, and phytotoxic activity. A simple and efficient synthesis of the macrocyclic dilactone, (-)-1-tetrahydropyrenophorol, has been accomplished from commercially available compounds. The synthesis utilizes regioselective ring opening of a chiral epoxide, followed by asymmetric dihydroxylation and a Mitsunobu reaction for the construction of the macrolactone.