CARBON AND OXYGEN ANALOGS OF PENICILLIN

摘要

In accordance with this invention, it has been found that oxygen analogs of 6.beta.-aminopenicillanic acid and biologically active derivatives thereof can be formed from esters of 6-oxo-penicillanic acid. For example, 6.beta.-phenoxyacetoxypenicillanic acid - an oxygen analog of penicillin V may be formed from an ester of 6-oxopenicillanate. The ester of 6-oxopenicillanic acid is formed by a diiospropyl carbodiimide/dimethyl sulfoxide oxidation of the corresponding ester of 6.alpha.-hydroxypenicillanic acid. The oxygen analogs are formed by reducing the ester of 6-oxo-penicillanic acid to the corresponding 6.beta.-hydroxypenicillanate and then forming the desired analog by acylation.