Diastereo- and enantioselective synthesis of allylsilane. A useful C-ring fragment of taxol

Article abstract of DOI:10.1016/S0040-4039(97)00843-5

Enantioselective synthesis of a taxol C-ring fragment containing an allylsilane moiety is described. Diastereoselective [4 + 2] cycloaddition of the pyrone with (R)-t-butylbenzyl vinyl ether followed by appropriate transformations gave a mixture of two regioisomeric cyclohexenyl sulfides, which was converted It, the title compound with almost complete diastereo- and enantioselectivities by treating with Li and 4,4'-di-t-butylbiphenyl followed by quenching with chlorotrimethylsilane.