Enantioselective Synthesis of (-)-Vertinolide

Abstract

(-)-Vertinolide, a β-tetronic acid derivative isolated from Verticillium intertextum as one of the mycotoxins, was synthesized starting from (R)-lactic acid as the chiral source by using Seebach's chiral self-reproduction method. The β-tetronic acid moiety was constructed by reductive dehydroxylation of α, β-dihydroxybutanolide with samarium(II) iodide and subsequent oxdation.