Asymmetric synthesis of the new marine epoxy lipid, (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol

An efficient and stereocontrolled process is described for the preparation of (6S, 7S, 9S, 10S)-6,9-epoxynonadee-18-ene-7.10-diol, a marine epoxy lipi d isolated from the brown alga, Notheia anomala. The key 2,3,5-trisubstitut ed tetrahydrofuran ring was constructed by stereoselective hydrogenation of the hemiketal derivative elaborated through nucleophilic addition of Grign ard reagent in the presence of CeCl3 to the highly functionalized lactone d erived from L-galactono-1,4-lactone,4-lactone. (C) 2001 Elsevier Science Lt d. All rights reserved.