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Total synthesis of a novel 2-thiabicyclo[3.2.0]heptan-6-one analogue of penicillin N |
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| Authors: | Amanda C FergusonRobert M Adlington Domnic H MartyresPeter J Rutledge Andrew CowleyJack E Baldwin |
| Institution: | a The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, UK b Boehringer-Ingelheim Pharma, Biberach, Germany c Department of Chemistry, The Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland d Chemical Crystallography Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, UK |
| Abstract: | 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-thiabicyclo3.2.0]heptan-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 and the introduction of nitrogen at C7 via an intramolecular nitrene insertion. |
| Keywords: | cycloaddition ketene β-lactam nitrene penicillin DAOCS |
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