First Synthetic Access to 6-(Methylene)oxapenems: A New Class of β-Lactamase Inhibitors

Abstract
The first synthetic route to racemic 6-(substituted methylene)oxapenems, an interesting new class of ß-lactamase inhibitors, is described. In spite of their low hydrolytic stability, even the unprotected acids 9 and 10 can be isolated as their sodium salts. The 6-(unsubstituted methylene)oxapenem 7e, however, is unstable and decomposes under the conditions of its formation.

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