Stereoselective synthesis of (-)-tetrahydropyrenophorol

Abstract

Tetrahydropyrenophorol, an interesting macrodiolide, was isolated from the plant Fagonia cretica. The total synthesis of (–)-1-tetrahydropyrenophorol was achieved in an elegant and linear manner from readily an accessible racemic epoxide. The archetypal reactions include regioselective opening of the epoxide, Sharpless asymmetric dihydroxylation, and Mitsunobu cyclodimerization to construct the requisite 16-membered bis-lactone. The synthetic approach demonstrated here is very simple and could be used for the syntheses of related compounds in an economic and highly stereoselective way.

Keywords

• macrodiolide
• sharpless asymmetric dihydroxylation
• mitsunobu reaction
• stereoselectivity