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Synthesis 1992; 1992(11): 1099-1103
DOI: 10.1055/s-1992-26314
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First Synthetic Access to 6-(Methylene)oxapenems: A New Class of ß-Lactamase Inhibitors

Hanno Wild* , Wolfgang Hartwig
  • *Bayer AG, Chemistry Science Laboratories Pharma, P. O. Box 101 709, D-5600 Wuppertal 1, Germany
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Publication Date:
17 September 2002 (online)

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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.