Helvetica Chimica Acta p. 1303 - 1311 (1981)
Update date:2022-08-03
Topics:
Ernest, Ivan
Main, Alan J.
Woodward, Robert B.
Selective formation - in intramolecular Wittig condensations - of the 2-oxocephem-4-carboxylate 8a and of the 2-acetylpenem-3-carboxylate 9, respectively, was observed as a consequence of different carbonyl reactivities in two homologous α-oxoacylthio groupings.Free, racemic and 7-unsubstituted 2-oxocephem-4-carboxylic acid (10) was prepared from 8a for biological testing.Attempts to prepare the free 2-acetylpenem-3-carboxylic acid from 9 failed, probably due to the high lability of the β-lactam system.
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