Nuclear analogs of β-lactam antibiotics. XI. Synthesis of 3-methyl-7-β-(phenoxyacetamido)-Δ3-desthiocephem-4-carboxylic acid

Abstract
Treatment of an acid with triethylamine in refluxing tert-butyl alcohol gave the decarboxylated product, which was isomerized to the desired .DELTA.3 isomer using DBN [1,5-diazabicyclo[4.3.0]-5-nonene]. Reduction of the azido functions followed by coupling to phenoxyacetic acid and debenzylation gave 2 acids. Attempts to prepare dienic cephalosporins failed. The halogenation of 2 compounds was studied and discussed.

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