Katsuki-Jacobsen oxidation-epoxidation of α-silyloxy sulfinyl dienes: application to the formal synthesis of (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol

The Katsuki-Jacobsen oxidation-epoxidation of acyclic α-silyloxy sulfinyl dienes, followed by acid-promoted cyclization, leads to 2,5-trans sulfonyl dihydrofurans with good selectivities. As an application, the formal synthesis of (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol is reported.