Syn-β-Hydroxyallylic Silanes from Terminal Epoxide α-Lithiation–Silylation and Alkenylation: Application to the Tetrahydrofuran Portion of the Lytophilippines

Abstract

Lithiation-in situ silylation of terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide in combination with phenyldimethyl(or diethyl)silyl chloride provides a direct process for the synthesis of trans-α,β-epoxysilanes, which undergo α-ring opening with alkenylcoppers to give syn-β-hydroxyallylic silanes. The chemistry is applied in an annulation approach to the C(10)-C(19) tetrahydrofuran-containing portion of the lytophilippines.