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Synlett 1990; 1990(11): 681-683
DOI: 10.1055/s-1990-21210
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Bridged Oxacephems; Part 1. Synthesis of 7α-[(R)-1-Hydroxyethyl]-2β,7β-ethano-1-oxacephems1,2

Masayuki Murakami* , Munenori Matsuura, Tsutomu Aoki, Wataru Nagata
  • *Shionogi Research Laboratories, Shionogy & Co., Ltd., Fukushima-ku, Osaka 553, Japan
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Publication Date:
08 March 2002 (online)

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Highly strained, bridged oxacephem molecules with the thienamycin-type [(R)-1-hydroxyethyl] side chain at 7α, 4 and 5, were designed as possible β-lactam antibiotics. Among them, two ethano-bridged compounds, i.e. 2β,7β-ethano-1-oxacephem 18 and its N-acetylcysteaminyl derivative 21, were successfully synthesized. X-ray crystallography showed that the distortion in the oxacephem moiety was comparable to the penicillin nucleus as indicated by the h value of 0.40 Å. As suggested by this value, the antibacterial activity of 21 was very weak.