Total Synthesis of cis-Solamin

A convergent total synthesis of cis-solamin and its diastereomer was accomplished using VO(acac)₂-catalyzed diastereoselective epoxidation followed by cyclization of bis-homoallylic alcohol as the key step. By comparison of the optical rotation of two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a.