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A route has been developed which allows synthesis of novel cyclobutanone analogues of penicillin. This is illustrated by the synthesis of (1R,4R,5R,5'R,7S)-(1b) and (1S,4S,5S,5'R,7R)-7-[5'-amino-5'-carboxy]pentanamido]-2-thiabicyclo[3.2.0]he ptan-6-one-4-carboxylate (1a), an analogue of penicillin N. The key steps in the synthesis were the formation of the bicyclic structure via a [2+2] cycloaddition...
Synthesis of (1SR, 4SR, 5SR, 7RS)-7-(tert-butoxycarbonylamino)-2-thiabicyclo[3.2.0]heptan-6-one-4-carboxy lic acid ethyl ester, a novel cyclobutanone analogue of a β-lactam antibiotic is described. This was achieved by [2+2] cycloaddition of a 2,3-dihydrothiophene with dichloroketene, followed by conversion to a cyclobutanol and use of an intramolecular nitrene insertion strategy to install nitrogen...
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