Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I

A convergent total synthesis of cis-solamin () and its diastereomer () was accomplished. A key reaction of this approach was the use of VO(acac)2-catalyzed diastereoselective epoxidation of (Z)-bis-homoallylic alcohol followed by spontaneous cyclization for the cis-THF ring formation. By comparison of the optical rotation of the two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is . Inhibitory action of synthetic and with bovine heart mitochondrial complex I are reported.