syn-β-Hydroxyallylic silanes from terminal epoxide α-lithiation-silylation and alkenylation: application to the tetrahydrofuran portion of the lytophilippines.
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.
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
David M
DM
Hodgson
Saifullah
S
Salik