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Synthesis of Enantiomerically Pure 2-Isoxacephems

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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

(αR,6R,7R)-7-(1-Acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylic acid and its enantiomer have been prepared. The ring systems were formed from the corresponding enantiomerically pure N-unsubstituted β-lactams. The reduction of methyl [(αR,2S,3R)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate] has been solved via a hemi-acetal. The structure and the configuration of a new stereogenic center in this intermediate was predicted by using 2D NMR technique and unambiguously proven by x-ray.

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Authors and Affiliations

  1. Institute for Organic Chemistry, Budapest University of Technology and Economics, P.O. Box 91, H-1521, Budapest, Hungary

    Zsuzsanna Sánta, József Nagy & József Nyitrai

  2. Institute of Chemistry, Chemical Research Center of Hungarian Academy of Sciences, H-1525, Budapest, Hungary

    László Párkányi

Authors
  1. Zsuzsanna Sánta
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  2. József Nagy
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  3. László Párkányi
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  4. József Nyitrai
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Correspondence to József Nyitrai.

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Sánta, Z., Nagy, J., Párkányi, L. et al. Synthesis of Enantiomerically Pure 2-Isoxacephems. Monatshefte für Chemie 135, 671–684 (2004). https://doi.org/10.1007/s00706-003-0135-9

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  • DOI: https://doi.org/10.1007/s00706-003-0135-9

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