Synthesis of the 1,2-Anti Type of 3E-Alkene-1,2,5-triol Derivatives

Abstract

We invented an efficient method to obtain 3E-alkene-1,2,5-triol derivatives with 1,2-anti stereochemistry from the 2Z,4E-alkadienyl alcohol derivatives, which were synthesized by using nickel-catalyzed coupling between lithium 1E-alkenyl borates and 1-halo-1Z-alken-3-ols. The method involves (1) asymmetric dihydroxylation at the E olefin moiety of the dienyl alcohol derivatives followed by formation of a cyclic carbonates; (2) palladium-catalyzed reaction with AcOH in the presence of Et 3 N. The method was applied successfully to the synthesis of the C6―C20 part of trioxilin A 3 .