Stereoselective Total Synthesis of Rhoiptelol B via Prins Cyclization

The stereoselective total synthesis of rhoiptelol B, a diaryl­heptanoid isolated from Rhoiptelea chiliantha 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.