Helvetica Chimica Acta · 1974 · 40 citations · 9 references
Natural SciencesChemistryMedicinal ChemistryBioorganic ChemistryDrug DiscoveryOrganic ChemistryAntibiotic ResistanceBeta-lactam ResistanceOrganic SynthesisAntibiotic DiscoveryLactam SynthesisTransformationsβ-Lactam Antibiotics
Abstract 3‐Hydroxy‐ceph‐3‐em‐esters 5 a – c , versatile intermediates for the preparation of new β‐lactam antibiotics, were obtained by ozonolysis of the corresponding 3‐methylidene‐esters 3 a – c . Reduction and elimination gave the 3‐unsubstituted ester 13 ; derivatives 16 a – c and 20 – 22 resulted from O‐alkylation. The 3‐methoxy‐esters 16 a – c were converted into the corresponding acids 23 a – d . Several other transformations of the β‐ketoester system are described.
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R. D. G. Cooper, Paul V. Demarco, C. F. Murphy et al. · Journal of the Chemical Society C Organic · 1970 · 20 citations