Abstract: The lithihum (a-carbalkoxyvinyl) (2-thienyl) mixed higher order cyanocuprate, de-rived from ethyl propargylic ester with (n-C₁₃H₂₇) (2-thienyl)CuCNLi₂, reacted with cis-1-bromo-l-propylene under Pd (PPh₃)₄ catalysis to give a diene ester ethyl 1- (Z-propylidene)-1-E-hexadecenate. Then the target product (±)-litsenolide C₂ was stereoselectively synthe-sized by employing cis-dihydroxylation of the diene ester using a NMO-OsO₄ system as the oxidant and stereospecific lactonation by acidic catalyst. The ratio of Eto Zcarbon-carbon double bond is >98: 2, and the ratio of trans- and cis-disubstituted lactones is >95: 5.

Key words: (±)-Litsenolide C₂, Mixed higher order cyanocuprate, Stereoselective reaction, AHF