Aza-Achmatowicz route to novel cyanocarbacephems

Chemical Communications

Volumn , Issue 7, 1996, Pages 881-882

  Ciufolini, Marco A ^a   Dong, Qing ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; CARBACEPHEM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0029920442     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000881     Document Type: Article

References (22)

1. For leading references see: The Organic Chemistry of β-lactams, ed. G. I. Georg, VCH, New York, 1993.
2. E.g.: E. Tonin and A. Tomasz, Antimicrob. Agents Chemother., 1986, 30, 577; P. A. C. Maple, J. M. T. Hamilton-Miller and W. Brumfitt, Lancet, 1989, 537; T. Suzuki, K. Fujita and Y. Nagamachi, J. Antibiot., 1994, 47, 47.
3. E.g.: E. Tonin and A. Tomasz, Antimicrob. Agents Chemother., 1986, 30, 577; P. A. C. Maple, J. M. T. Hamilton-Miller and W. Brumfitt, Lancet, 1989, 537; T. Suzuki, K. Fujita and Y. Nagamachi, J. Antibiot., 1994, 47, 47.
4. E.g.: E. Tonin and A. Tomasz, Antimicrob. Agents Chemother., 1986, 30, 577; P. A. C. Maple, J. M. T. Hamilton-Miller and W. Brumfitt, Lancet, 1989, 537; T. Suzuki, K. Fujita and Y. Nagamachi, J. Antibiot., 1994, 47, 47.
5. E.g.: W. Dürckheimer, J. Blumbach, R. Lattrell and K. H. Scheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; H. Lode, M. Fassbender, T. Schaberg, K. Borner and P. Koeppe, Drugs, 1994, 47, suppl. 3, 10; H. Hanaki, H. Akagi, M. Yasui and T. Otani, J. Antibiot., 1995, 48, 901;
6. E.g.: W. Dürckheimer, J. Blumbach, R. Lattrell and K. H. Scheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; H. Lode, M. Fassbender, T. Schaberg, K. Borner and P. Koeppe, Drugs, 1994, 47, suppl. 3, 10; H. Hanaki, H. Akagi, M. Yasui and T. Otani, J. Antibiot., 1995, 48, 901;
7. E.g.: W. Dürckheimer, J. Blumbach, R. Lattrell and K. H. Scheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; H. Lode, M. Fassbender, T. Schaberg, K. Borner and P. Koeppe, Drugs, 1994, 47, suppl. 3, 10; H. Hanaki, H. Akagi, M. Yasui and T. Otani, J. Antibiot., 1995, 48, 901;
8. The first carbacephem was described by: R. N. Guthikonda, L. D. Cama and B. G. Christensen, J. Am. Chem. Soc., 1974, 96, 7584. For leading references see, e.g.: P. R. Guzzo and M. J. Miller, J. Org. Chem., 1994, 59, 4862; S. Hanessian and G. B. Reddy, Bioorg. Med. Chem. Lett., 1994, 4, 2285 and references cited therein; H. Saito, F. Suzuki and T. Hirata, Chem. Pharm. Bull., 1989, 37, 2298.
9. The first carbacephem was described by: R. N. Guthikonda, L. D. Cama and B. G. Christensen, J. Am. Chem. Soc., 1974, 96, 7584. For leading references see, e.g.: P. R. Guzzo and M. J. Miller, J. Org. Chem., 1994, 59, 4862; S. Hanessian and G. B. Reddy, Bioorg. Med. Chem. Lett., 1994, 4, 2285 and references cited therein; H. Saito, F. Suzuki and T. Hirata, Chem. Pharm. Bull., 1989, 37, 2298.
10. The first carbacephem was described by: R. N. Guthikonda, L. D. Cama and B. G. Christensen, J. Am. Chem. Soc., 1974, 96, 7584. For leading references see, e.g.: P. R. Guzzo and M. J. Miller, J. Org. Chem., 1994, 59, 4862; S. Hanessian and G. B. Reddy, Bioorg. Med. Chem. Lett., 1994, 4, 2285 and references cited therein; H. Saito, F. Suzuki and T. Hirata, Chem. Pharm. Bull., 1989, 37, 2298.
11. The first carbacephem was described by: R. N. Guthikonda, L. D. Cama and B. G. Christensen, J. Am. Chem. Soc., 1974, 96, 7584. For leading references see, e.g.: P. R. Guzzo and M. J. Miller, J. Org. Chem., 1994, 59, 4862; S. Hanessian and G. B. Reddy, Bioorg. Med. Chem. Lett., 1994, 4, 2285 and references cited therein; H. Saito, F. Suzuki and T. Hirata, Chem. Pharm. Bull., 1989, 37, 2298.
12. Cf. C. C. Bodurow, B. D. Boyer, C. A. Brennan, C. A. Bunnell, J. E. Burks, M. A. Carr, C. W. Doecke, T. M. Eckrich, J. M. Fischer, J. P. Gardner, B. J. Graves, P. Hines, R. C. Hoying, B. G. Jackson, M. D. Kinnick, C. D. Kochert, J. S. Lewis, W. D. Luke, L.L. Moore, J. M. Morin, Jr., N. L. Nist, D. E. Prather, D. L. Sparks and W. C. Vladuchick, Tetrahedron Lett., 1989, 30, 2321.
13. M. A. Ciufolini, C. W. Hermann, K. H. Whitmire and N. E. Byrne, J. Am. Chem. Soc., 1989, 111, 3473.
14. D. G. Drueckhammer, C. F. Barbas, III. K. Nozaki, C. H. Wong, C. Y. Wood and M. A. Ciufolini, J. Org. Chem., 1988, 53, 1607.
15. A. K. Bose, J. C. Kapur, S. D. Sharma and M. S. Manhas, Tetrahedron Lett., 1973, 14, 2319; G. I. Georg, P. He, J. Kant and Z.-J. Wu, J. Org. Chem., 1993, 58, 5771 and references cited therein.
16. A. K. Bose, J. C. Kapur, S. D. Sharma and M. S. Manhas, Tetrahedron Lett., 1973, 14, 2319; G. I. Georg, P. He, J. Kant and Z.-J. Wu, J. Org. Chem., 1993, 58, 5771 and references cited therein.
17. T. Fukuyama, R. K. Frank and C. F. Jewell, J. Am. Chem. Soc., 1980, 102, 2122; T. Fukuyama, A. A. Laird and L. M. Hotchkiss, Tetrahedron Lett., 1985, 26, 6291.
18. T. Fukuyama, R. K. Frank and C. F. Jewell, J. Am. Chem. Soc., 1980, 102, 2122; T. Fukuyama, A. A. Laird and L. M. Hotchkiss, Tetrahedron Lett., 1985, 26, 6291.
19. N. D. Kimp, R. Verhé, L. De Buyck and N. Schamp, Chem. Ber., 1983, 116, 3846; H. Ahlbrecht and D. Liesching, Synthesis, 1977, 495.
20. N. D. Kimp, R. Verhé, L. De Buyck and N. Schamp, Chem. Ber., 1983, 116, 3846; H. Ahlbrecht and D. Liesching, Synthesis, 1977, 495.
21. M. Miyashita, A. Yoshikoshi and P. A. Grieco, J. Org. Chem., 1977, 42, 3772.
22. V. Asher, C. Becu, M. J. O. Anteunis and R. Callens, Tetrahedron Lett., 1981, 22, 141.