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Issue 14, 2003
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Application of the Barton photochemical reaction in the synthesis of 1-dethia-3-aza-1-carba-2-oxacephem: a novel agent against resistant pathogenic microorganisms

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Abstract

Racemic 7-(phenylacetamido)-1-dethia-3-aza-1-carba-2-oxacephem 3 was synthesized and found to possess antibacterial activity against Staphylococcus aureus FDA 209P, Escherichia coli ATCC 39188, Pseudomonas aeruginosa 1101–75 and Klebsiella pneumoniae NCTC 418 as well as the β-lactamase producing organisms E. coli A9675 and P. aeruginosa 18S-H and the methicillin-resistant organism S. aureus 95. Formation of the carbacephem 3 originated from the Barton photochemical reaction in the conversion of 8 to 10. Intramolecular cyclization of syn-oximino β-lactam 10 afforded 7-azido-2-oxa-3-azacephem 11, which was reduced and acylated to 12. Enzymatic removal of the methyl group from 12 gave the target molecule 3.

Graphical abstract: Application of the Barton photochemical reaction in the synthesis of 1-dethia-3-aza-1-carba-2-oxacephem: a novel agent against resistant pathogenic microorganisms

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Publication details

The article was received on 23 Apr 2003, accepted on 30 May 2003 and first published on 12 Jun 2003


Article type: Paper
DOI: 10.1039/B304167K
Org. Biomol. Chem., 2003,1, 2461-2467

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    Application of the Barton photochemical reaction in the synthesis of 1-dethia-3-aza-1-carba-2-oxacephem: a novel agent against resistant pathogenic microorganisms

    G. H. Hakimelahi, P. Li, A. A. Moosavi-Movahedi, J. Chamani, G. A. Khodarahmi, T. Wei Ly, F. Valiyev, M. K. Leong, S. Hakimelahi, K. Shia and I. Chao, Org. Biomol. Chem., 2003, 1, 2461
    DOI: 10.1039/B304167K

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