β-Lactams via aα,β-Unsaturated Acid Chlorides: Intermediates for Carbapenem Antibiotics1

Journal of Organic Chemistry

Volumn 55, Issue 2, 1990, Pages 575-580

  Manhas, M S ^a   Ghosh, Malay ^a   Bose, Ajay K ^a  

^a STEVENS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0025099582     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00289a035     Document Type: Article

References (40)

1. Studies on Lactams. Part 84; for part 83, see: van der Veen, J. M.; Bari, S. S.; Krishnan, L.; Manhas, M. S.; Bose, A. K. J. Org, Chem. 1989, 54, 5758.
2. For reviews, see: (a) Manhas, M. S.; Bose, A. K. Beta-lactams-Natural and Synthetic; Wiley Interscience: New York, 1971.
3. Chemistry and Biology of Beta Lactam antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vol. 2.
4. Koppel, G. A. In Small Ring Heterocycles; Hassner, A., Ed.; John Wiley: New York, 1983; Part 2, pp 248–301.
5. Manhas, M. S.; Van der Veen, J. M.; Wagle, D. R.; Hedge, V. R.; Bari, S. S.; Kosarych, Z.; Ghosh, M.; Krishnan, L. Indian J. Chem. 1986, 25B, 1095.
6. Vanderhaeghe, H.; Thomis, J. J. Med. Chem. 1975, 18, 486.
7. Bachi, M. D.; Sasson, S.; Vaya, J. J. Chem. Soc., Perkin Trans. 1 1980. 2228.
8. Firestone, R. A.; Maciejewicz, N. S.; Christensen, B. G. J. Org. Chem. 1974. 39. 3384.
9. Edwards, J. A.; Guzman, A.; Johnson, R.: Beeby, P. J.; Fried, J. H. Tetrahedron Lett. 1974, 2031.
10. Hashimoto, T.; Watanabe, T.; Kawano, Y.; Tanaka, T.; Miyadera, T. Chem, Pharm. Bull. 1980, 28, 2980.
11. Kamiya, T.; Oku, T.; Nakaguchi, O.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1978, 5119.
12. For a detailed account, see: Holden, K. G. In Chemistry and Biology of Beta-lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vol. 2, p 101.
13. Bose, A. K.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett. 1971, 3167.
14. Zamboni, R.; Just, G. Can. J. Chem. 1979, 57, 1945.
15. Bose, A. K.; Krishnan, L.; Wagle, D. R.; Manhas, M. S. Tetrahedron Lett. 1986, 27, 5955.
16. Bouffard, F. A.; Johnston, D. B. R.; Christensen, B. G. J. Org. Chem. 1980, 45, 1130.
17. Pfaendler, H. R.; Gosteli, J.; Woodward, R. B. J. Am. Chem. Soc. 1980, 102, 2039.
18. Yoshida, A.; Hayashi, T.; Takeda, N.; Oida, S.; Ohki, E. Chem. Pharm. Bull. 1981, 29, 2899.
19. Martel, A.; Collerette, J.; Banville, J.; Daris, J. P.; Lapointe, P.; Belleau, B.; Menard, M. Can. J. Chem. 1983, 61, 613.
20. Odriozola, J. M.; Cossio, F. P.; Palomo, C. J. Chem. Soc., Chem. Commun. 1988, 809.
21. Cossio, F. P.; Odriozola, J. M.; Oiarbide, M.; Palomo, C. J. Chem. Soc., Chem. Commun. 1989. 74.
22. Sato, M.; Ogasawara, H.; Takayama, K.; Kaneko, C. Heterocycles 1987. 26, 2611.
23. Georg, G. I. Tetrahedron Lett. 1984, 25, 3779.
24. Hart, D. J.; Lee, C.; Pirkle, W. H.; Hyou, M. H.; Tsipouras, A. J. Am. Chem. Soc. 1986, 108, 6054.
25. Ha, D.; Hart, D. J. J. Antibiot. 1987, 40, 309.
26. Hart, D. J.; Ha, D. Tetrahedron Lett. 1985, 26, 5493.
27. Georg, G. I.; Gill, H. S. J. Chem. Soc., Chem. Commun. 1985, 1433.
28. Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 109, 1129.
29. George, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692.
30. Georg, G. I. In Synthesis of Thiena-mycin and Related Beta-Lactams from 3-Hydroxybutyric Acid; Atta-ur-Rahaman, Ed.; Elsevier Science: Amsterdam, Vol 2, in press.
31. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
32. Kametani, T.; Honda, T.; Nakayama, A.; Fukumoto, K. Heterocycles 1980, 14, 1967.
33. Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 496.
34. Buynak, J. D.; Rao, M. N.; Pajouhesh, H.; Chandrasekaran, R. Y.; Finn, K., deMeester, P.; Chu, S. C. J. Org. Chem. 1985, 50, 4245.
35. For similar type of work, see: (a) Buynak, J. D.; Rao, M. N.; Chandrasekran, R. Y.; Haley, E.; deMeester, P.; Chu, S. C. Tetrahedron Lett. 1985, 26, 5001.
36. Buynak, J. D.; Narayana Rao, M. J. Org. Chem. 1986, 51, 1571.
37. Buynak, J. D.; Mathew, J.; Narayana Rao, M.; Haley, E.; George, C.; Siriwardane, U. J. Chem. Soc., Chem. Commun. 1987, 735.
38. Fetter, J.; Lempert, K.; Gigur, T.; Nyitrai, J.; Kajtar-Peredy, M.; Simig, G.; Hornyak, G.; Doleschall, G. J. Chem. Soc., Perkin Trans. 1 1986, 221.
39. Fetter, J.; Lempert, K.; Kajtar-Peredy, M.; Simig, G.; Hornyak, G. J. Chem.Soc., Perkin Trans. 1 1986, 1453.
40. Fetter, J.; Lempert, K.; Horvath, Z.; Kajtar-Peredy, M.; Simig, G.; Hornyak, G. J. Chem. Res. 1985 (S), 368.