Abstract
An efficient and stereocontrolled process is described for the preparation of (6 S,7 S,9 S,10 S)-6,9-epoxynonadec-18-ene-7,10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala. The key 2,3,5-trisubstituted tetrahydrofuran ring was constructed by stereoselective hydrogenation of the hemiketal derivative elaborated through nucleophilic addition of Grignard reagent in the presence of CeCl 3 to the highly functionalized lactone derived from L-galactono-1,4-lactone.
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