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Issue 1, 2001
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An approach to the synthesis of 5,5-trans-fused lactam analogues of β-lactam antibiotics

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Abstract

A racemic synthesis of two diastereoisomeric α-benzyloxycarbonylamino substituted trans-fused bicyclic lactams (4 and 5), was achieved from cyclopentene oxide. These lactams are useful intermediates to investigate the possibility of using a trans-lactam template as a replacement for the β-lactam ring found in conventional antibacterial agents. One of the intermediates (4) was further elaborated to an analogue of the antibacterial agent ceftazidime.

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Publication details

The article was received on 08 Sep 2000, accepted on 27 Oct 2000 and first published on 05 Dec 2000


Article type: Paper
DOI: 10.1039/B007286I
Citation: J. Chem. Soc., Perkin Trans. 1, 2001, 21-25
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    An approach to the synthesis of 5,5-trans-fused lactam analogues of β-lactam antibiotics

    P. W. Smith, A. R. Whittington, K. N. Cobley, A. Jaxa-Chamiec and H. Finch, J. Chem. Soc., Perkin Trans. 1, 2001, 21
    DOI: 10.1039/B007286I

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