Stereoselective Total Synthesis of Rhoiptelol B via Prins Cyclization

Abstract

The stereoselective total synthesis of rhoiptelol B, a diaryl­heptanoid isolated from <i>Rhoiptelea chiliantha</i> is described. The tetrahydropyran ring was constructed by using Prins cyclization. The key steps involved in this synthesis are Prins cyclization, Mistunobu inversion, cross metathesis, Sharpless asymmetric dihydroxylation, and hydrogenolysis.