Ring Opening of a meso-Azabicyclic Alkene with an Arylboronic Acid

Significance

The first enantioselective total synthesis of the biologically important (+)-homochelidonine was accomplished utilizing an excellent desymmetrization of a meso-bicylic alkene based on a palladium-catalyzed ring-opening reaction. This method creates two contiguous syn stereocenters from readily available meso compounds. Once this chirality is installed, subsequent diastereoselective bromohydrin formation leading to an epoxide is expertly accomplished.