Stereocontrolled synthesis of 2-alkenyl-4-methylene tetrahydropyrans

A variety of 2-alkenyl-4-methylene tetrahydropyrans were synthesized via consecutive transition metal-catalyzed bond forming processes. In this approach, ruthenium-catalyzed coupling of homoallylic carbonates and homopropargylic alcohols generates substrates containing the requisite functionality for a palladium-mediated cyclization, thereby providing concise access to the target structures. The installation of a trisubstituted alkene at the C-2 position was achieved using an olefin cross metathesis process.