Oxidative Free-Radical Cyclization as a Method for Annulating β-Lactams: Syntheses of Functionalized Carbacephams

Journal of Organic Chemistry

Volumn 60, Issue 19, 1995, Pages 6176-6179

  Crocker, Peter J ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBACEPHEM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0028792629     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00124a035     Document Type: Note

References (34)

1. Guzzo, P. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4862.
2. Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618.
3. Miller, M. J. Acc. Chem. Res. 1986, 19, 49.
4. Teng, M.; Miller, M. J.; Nicas, T. I.; Grissom-Arnold, J.; Cooper, R. D. G. Bioorg. Med. Chem. 1993, 1, 151.
5. Bulychev, A.; O’Brien, M. E.; Massova, I.; Teng, M.; Gibson, T. A.; Miller, M. J.; Mobashery, S. J. Am. Chem. Soc. 1995, 117, 5938.
6. Davies, J. Science 1994, 264, 375.
7. Brown, A. G.; Pearson, M. J.; Southgate, R. In Comprehensive Medicinal Chemistry, Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 2, pp 662-671.
8. Miller, M. J.; Malouin, F. Acc. Chem. Res. 1993, 26, 241.
9. Miller, M. J. Chem. Rev. 1989, 89, 1563.
10. Sato, K.; Okachi, R.; Matsukuma, I.; Mochida, K.; Hirata, T. J. Antibiot. 1989, 42, 1844.
11. Matsukuma, I.; Yoshiiye, S.; Mochida, K.; Hashimoto, Y.; Sato, K.; Okachi, R.; Hirata, T. Chem. Pharm. Bull. 1989, 37, 1239.
12. Frazier, J. W.; Staszak, M. A.; Weigel, L. O. Tetrahedron Lett. 1992, 33, 857.
13. Pasini, C. E.; Indelicato, J. M. Pharm. Res. 1992, 9, 250.
14. Blaszczak, L. C.; Brown, R. F.; Cook, G. K.; Hornback, W. J.; Hoying, R. C.; Indelicato, J. M.; Jordan, C. L.; Katner, A. S.; Kinnick, M. D.; McDonald, J. H., III; Morin, J. M., Jr.; Munroe, J. E.; Pasini, C. E. J. Med. Chem. 1990, 33, 1656.
15. Cooper, R. D. G. In The Chemistry of Beta-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8.
16. Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; Chapter 3.
17. Bachi, M. D.; Froloŵ, F.; Hoornaert, C. J. Org. Chem. 1983, 58, 1841.
18. Bosch, E.; Bachi, M. D. J. Org. Chem. 1993, 48, 5581.
19. Mochida, K.; Hirata, T. Chem. Pharm. Bull. 1988, 36, 3642.
20. Crocker, P. J.; Karlsson-Andreasson, U.; Lotz, B. T.; Miller, M. J. Heterocycles 1995, 40, 691.
21. Ernest, I.; Gosteli, J.; Greengrass, C. W.; Holick, W.; Jackman, D. E.; Pfaendler, H. R.; Woodward, R. B. J. Am. Chem. Soc. 1978, 100, 8214.
22. Huang, N. Z.; Kalish, V. J.; Miller, M. J. Tetrahedron 1990, 46, 8067.
23. Jackson, B. G.; Gardner, J. P.; Heath, P. C. Tetrahedron Lett. 1990, 31, 6317.
24. Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161.
25. Wasserman, H. H.; Han, W. T. Tetrahedron Lett. 1984, 25, 3743 and 3747.
26. Kates, S. A.; Dombroski, M. A.; Snider, B. B. J. Org. Chem. 1990, 55, 2427.
27. Snider, B. B.; Merritt, J. E. Tetrahedron 1991, 47, 8663.
28. Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1991, 56, 5544.
29. Curran, D. P. in Comprehensive Organic Chemistry, Trost, B. M., Fleming, I.; Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapters 4. 1 and 4. 2.
30. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1986.
31. Melikyan, G. G. Synthesis 1993, 833.
32. Citterio, A.; Marion, A.; Maronati, A.; Nicolini, M. Tetrahedron Lett. 1993, 34, 7981.
33. Peterson, J. R.; Egler, R. S.; Horsley, D. B.; Winter, T. J. Tetrahedron Lett. 1987, 28, 6109.
34. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.