The total synthesis of a nuclear analogue of the penicillin—cephalosporin antibiotics
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 3756-3762
- https://doi.org/10.1039/j39710003756
Abstract
A route has been developed for the synthesis of nuclear analogues of the penicillins and cephalosporins from heterocyclic α-amino-acids. The route is illustrated by the synthesis of (2R,6R,7S)-8-oxo-7-phenylacetamido-1-azabicyclo[4,2,0]octane-2-carboxylic acid (19) from pyridine-2-carboxylic acid. A key step in the synthesis involves the photolysis of a diazo-compound and stereoselective intramolecular insertion by the transient carbene intermediate, so generating the required fused β-lactam heterocyclic system.Keywords
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