Synthesis of (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala, by an oxiranyl anion strategy

Article abstract of DOI:10.1016/S0040-4039(98)02441-1

The stereocontrolled synthesis of (6S,7S,9R,10R)-6,9-epoxynonadec-18- ene-7,10-diol, isolated from the brown alga, Notheia anomala, has been achieved. The key 2,3,5-trisubstituted tetrahydrofuran ring was constructed by alkylation of the sulfonyl-stabilized oxiranly anion followed by 5-endo cyclization.