Stereocontrolled synthesis of polycyclic ethers and related heterocycles via the intramolecular reaction of allylstannanes

The synthetic reaction using functionalized allylstannanes is widely appreciated as one of the most useful methods for the stereocontrolled C-C bond formation. We now report the stereoselective synthesis of functionalized heterocycles via the intramolecular reaction of allylstannane with aldehydes and imines. The stereocontrolled total synthesis of hemibrevetoxin B was achieved by using the intramolecular reaction of γ-alkoxyallylstannane with aldehydes. The extension of this methodology led to a new strategy for the stereoselective synthesis of alkaloids such as (+)-desoxoprosopinine and (+)-preussin.