Abstract
A convergent total synthesis of cis-solamin ( 1a ) and its diastereomer ( 1b ) was accomplished. A key reaction of this approach was the use of VO(acac) 2-catalyzed diastereoselective epoxidation of ( Z)-bis-homoallylic alcohol 3 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 1a . Inhibitory action of synthetic 1a and 1b with bovine heart mitochondrial complex I are reported.
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