Synthesis of (3,4) β-methylenecepham and (3,4) β-methylene-carbacepham via intramolecular carbene addition to double bond

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 9, 2003, Pages 1957-1967

  Korda, Anna ^a   Winiarski, Jerzy ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; CARBENE; CEPHAM DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CHEMICAL BOND; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; KLEBSIELLA PNEUMONIAE; MORGANELLA MORGANII; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROVIDENCIA RETTGERI; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

BACTERIA (MICROORGANISMS);

EID: 0037401369     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00084-1     Document Type: Article

References (17)

1. Keith D.D., Tengi J., Rossman P., Todaro L., Weigele M. Tetrahedron. 39:1983;2445.
2. Christensen, J.; Georgopapadakou, N.; Keith, D.; Luk, K.-C.; Madison, V.; Mook, R.; Pruess, D.; Roberts, J.; Rossman, P.; Wei, C.-C.; Weigele, M.; West, K. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Special Publication No. 70; Royal Society of Chemistry: London, 1989; p 33.
3. Wei C.C., Christenson J.G., Corraz A.J., Keith D.D. Bioorg. Med. Chem. 1:1991;43.
4. Kamiya T., Teraji T., Hashimoto M., Nakaguchi O., Oku T. J. Am. Chem. Soc. 97:1975;5020.
5. Bateson, J. H.; Corbett, D. F.; Southgate, R. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Brown, A.G., Roberts, S.M., Eds.; Special Publications No. 52: Royal Society of Chemistry: London, 1984; p 116.
6. Bateson J.H., Kaura A.C., Southgate R. Tetrahedron Lett. 32:1991;2065.
7. Bateson J.H., Southgate R., Tyler J.W., Fell S.C.M. J. Chem. Soc., Perkin Trans. 1. 1986;973.
8. Bateson J.H., Fell S.M., Kaura A.C., Arun C., Southgate R. J. Chem. Soc. Perkin Trans. 1. 13:1992;1577.
9. Long, A.G. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Elks, J., Ed.; Special Publications No. 28; The Chemical Society: London, 1977; p 214.
10. Branch L.C., Pearson M.J. J. Chem. Soc., Perkin Trans. 1. 1979;2268.
11. Lammert S.R., Kukolja S. J. Am. Chem. Soc. 97:1975;5583.
12. Mori M., Kanda N., Ban Y. J. Chem. Soc., Chem. Commun. 1986;1375.
13. Mori M., Kanda N., Ban Y., Aoe K. J. Chem. Soc., Chem. Commun. 1988;12.
14. Afonso A., Hon F., Weinstein J., Ganguly A.K., McPhail A.T. J. Am. Chem. Soc. 104:1982;6138.
15. Yoshida A., Hayashi T., Takeda N., Oida S., Okhi E. Chem. Pharm. Bull. 1983;768.
16. Kawamoto I., Endo R., Suzuki K., Hata T. Heterocycles. 25:1987;123.
17. Crystallographic data (excluding structure factors) for structure 6a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 196221. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).