Synthesis of cephems bearing olefinic sulfoxide side chains as potential β-lactamase inhibitors

Several cephems bearing vinyl sulfoxide and sulfone moieties at C-3 were prepared by the Stille coupling of a 3-trifloxy cephem with stannanes. The sulfoxides were designed to be suicide lactamase inhibitors. None of the cephems described in this study functioned as an enzyme inhibitor, but two derivatives displayed interesting biological activity against Methycillin - resistant S. Aureus.