Carbon and oxygen analogs of penicillin

摘要

In accordance with this invention, it has been found that carbon and oxygen analogs of 6 beta -aminopenicillanic acid and biologically active derivatives thereof can be formed from esters of 6-oxopenicillanic acid. For example, 6 beta -phenoxyacetoxy-penicillanic acid-an oxygen analog of penicillin V and 6 beta -phenoxyacetylmethylpenicillanic acid-a carbon 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-oxopenicillanic acid to the corresponding 6 beta -hydroxypenicillanate and then forming the desired analog by acylation. The carbon analogs are formed by a Wittig reaction of the ester of 6-oxopenicillanic acid with a suitable acylmethylenetriphenylphosphorane followed by saturation of the newly formed double bond and removal of the protective ester group.