Stereoselective Synthesis of the Chiral Tetrahydropyrane Core of Swinholides and Misakinolides

Stereoselective synthesis of the optically pure tetrahydropyrane core of swinholides and misakinolide A starting from (5)-methyl lactate is described in which the highly stereoselective intramolecular iodoetherification for construction of the tetrahydropyrane ring and the regioselective ring-opening reaction of an epoxide are involved as key steps.