Halide-terminated N-acyliminium ion-alkyne cyclizations: A new construction of carbacephem antibiotics

Journal of Organic Chemistry

Volumn 62, Issue 26, 1997, Pages 9210-9216

  Metais, Eric ^a   Overman, Larry E ^a   Rodriguez, Maria Inés ^a,b   Stearns, Brian A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 (1 CHLOROETHYLIDENE)CARBACEPHEM; ACETIC ACID DERIVATIVE; AZETIDINONE DERIVATIVE; CARBACEPHEM DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; HALIDE; LORACARBEF; OZONE; PENICILLIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0031459058     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971433w     Document Type: Article

References (45)

1. (a) Christensen, B. G.; Guthikonda, R. N.; Cama, L. D. J. Am. Chem. Soc. 1974, 96, 7584.
2. (b) Firestone, R. A.; Fahey, J. L.; Maciejiwicz, N. S.; Christensen, B. G. J. Med. Chem. 1977, 20, 551.
3. Force, R. W.; Nahata, M. C. Ann. Pharmacotherapy 1993, 27, 321.
4. For reviews, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; pp 121-196. (b) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. L. Ed.; Chapman & Hall: London, 1992; pp 272-305.
5. For reviews, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; pp 121-196. (b) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. L. Ed.; Chapman & Hall: London, 1992; pp 272-305.
6. For recent contributions, see: (a) Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618. (b) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1993, 139. Bachi, M. D.; Bar-Ner, N. Biomed. Chem. 1993, 3, 2439. Teng, M.; Gasparski, C. M.; Williams, M. A.; Miller, M. J. Biomed. Chem. 1993, 3, 2431. (e) Guzzo, P. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4862.
7. For recent contributions, see: (a) Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618. (b) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1993, 139. Bachi, M. D.; Bar-Ner, N. Biomed. Chem. 1993, 3, 2439. Teng, M.; Gasparski, C. M.; Williams, M. A.; Miller, M. J. Biomed. Chem. 1993, 3, 2431. (e) Guzzo, P. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4862.
8. For recent contributions, see: (a) Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618. (b) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1993, 139. Bachi, M. D.; Bar-Ner, N. Biomed. Chem. 1993, 3, 2439. Teng, M.; Gasparski, C. M.; Williams, M. A.; Miller, M. J. Biomed. Chem. 1993, 3, 2431. (e) Guzzo, P. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4862.
9. For recent contributions, see: (a) Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618. (b) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1993, 139. Bachi, M. D.; Bar-Ner, N. Biomed. Chem. 1993, 3, 2439. Teng, M.; Gasparski, C. M.; Williams, M. A.; Miller, M. J. Biomed. Chem. 1993, 3, 2431. (e) Guzzo, P. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4862.
10. For recent contributions, see: (a) Lotz, B. T.; Miller, M. J. J. Org. Chem. 1993, 58, 618. (b) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1993, 139. Bachi, M. D.; Bar-Ner, N. Biomed. Chem. 1993, 3, 2439. Teng, M.; Gasparski, C. M.; Williams, M. A.; Miller, M. J. Biomed. Chem. 1993, 3, 2431. (e) Guzzo, P. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4862.
11. Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3787.
12. See, inter alia: (a) Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612. (b) Lin, N.-H.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9062. Caderas, C.; Lett, R.; Overman, L. E.; Rabinowitz, M. H.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9073.
13. See, inter alia: (a) Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612. (b) Lin, N.-H.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9062. Caderas, C.; Lett, R.; Overman, L. E.; Rabinowitz, M. H.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9073.
14. See, inter alia: (a) Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612. (b) Lin, N.-H.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9062. Caderas, C.; Lett, R.; Overman, L. E.; Rabinowitz, M. H.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9073.
15. Brosius, A. D.; Overman, L. E. J. Org. Chem. 1997, 62, 440.
16. The synthesis of bicyclic β-lactams by related free-radical cyclizations has been extensively developed by Bachi and co-workers, see: Bachi, M. D. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Bentley, P. H., Southgate, R., Eds.; Royal Society of Chemistry: London, 1990; pp 91-105.
17. For other examples of cyclizations of N-acyliminium cations derived from glyoxylates with tethered alkynes, see: Mooiweer H. H.; Hiemstra, H.; Fortgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 1987, 28, 3285.
18. (a) Scartazinni, R.; Bickel, H. Helv. Chim. Acta 1974, 57, 1919.
19. (b) Chauvette, R. R.; Pennington, P. A. J. Am. Chem. Soc. 1974, 96, 4986.
20. For a recent review of functional group transformations on the β-lactam nucleus see: Wild, H. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; pp 49-119.
21. For previous asymmetric total syntheses of loracarbef: (a) Bodurow, C. C.; Boyer, B. D.; Brennan, J.; Bunnell, C. A.; Burks, J. E.; Carr, M. A.; Doecke, C. W.; Eckrich, T. M.; Fisher, J. W.; Gardner, J. P.; Graves, B. J.; Hines, P.; Hoying, R. C.; Jackson, B. G.; Kinnick, M. D.; Kochert, C. D.; Lewis, J. S.; Luke, W. D.; Moore, L. L.; Morin, J. M., Jr.; Nist, R. L.; Prather, D. L.; Sparks, D. E.; Vladuchick W. C. Tetrahedron Lett. 1989, 30, 2321. (b) Frazier, J. W.; Staszak, M. A.; Weigel, L. O. Tetrahedron Lett. 1992, 33, 857.
22. For previous asymmetric total syntheses of loracarbef: (a) Bodurow, C. C.; Boyer, B. D.; Brennan, J.; Bunnell, C. A.; Burks, J. E.; Carr, M. A.; Doecke, C. W.; Eckrich, T. M.; Fisher, J. W.; Gardner, J. P.; Graves, B. J.; Hines, P.; Hoying, R. C.; Jackson, B. G.; Kinnick, M. D.; Kochert, C. D.; Lewis, J. S.; Luke, W. D.; Moore, L. L.; Morin, J. M., Jr.; Nist, R. L.; Prather, D. L.; Sparks, D. E.; Vladuchick W. C. Tetrahedron Lett. 1989, 30, 2321. (b) Frazier, J. W.; Staszak, M. A.; Weigel, L. O. Tetrahedron Lett. 1992, 33, 857.
23. Clauss, K.; Grimm, D.; Proesel, G. Liebigs Ann. Chem. 1974, 539.
24. (a) Mickel, S. Aldrichimica Acta 1985, 18, 95.
25. (b) Koller W.; Linkies, A.; Pietsch, H., Rehling, H.; Reuschling, D. Tetrahedron Lett. 1982, 23, 1545.
26. Bevilacqua, P.; Roberts, J. L. Synth. Commun. 1983, 10, 797.
27. Lipshutz, B. H.; Koerner, M.; Parker, D. A. Tetrahedron Lett. 1987, 28, 945.
28. Iodoalkynes 8 have been previously described. 8a: Hewson A. T.; MacPherson, D. T. J. Chem. Soc., Perkin Trans. 1 1985, 2625. 8b: Fisher, M. J.; Overman, L. E. J. Org. Chem. 1990, 55, 1447. 8c: Negishi, E.; Boardman, L. D.; Sawada, H.; Bagheri, V.; Stoll, A. T.; Tour, J. M.; Rand, C. L. J. Am. Chem. Soc. 1988, 110, 5383.
29. Iodoalkynes 8 have been previously described. 8a: Hewson A. T.; MacPherson, D. T. J. Chem. Soc., Perkin Trans. 1 1985, 2625. 8b: Fisher, M. J.; Overman, L. E. J. Org. Chem. 1990, 55, 1447. 8c: Negishi, E.; Boardman, L. D.; Sawada, H.; Bagheri, V.; Stoll, A. T.; Tour, J. M.; Rand, C. L. J. Am. Chem. Soc. 1988, 110, 5383.
30. Iodoalkynes 8 have been previously described. 8a: Hewson A. T.; MacPherson, D. T. J. Chem. Soc., Perkin Trans. 1 1985, 2625. 8b: Fisher, M. J.; Overman, L. E. J. Org. Chem. 1990, 55, 1447. 8c: Negishi, E.; Boardman, L. D.; Sawada, H.; Bagheri, V.; Stoll, A. T.; Tour, J. M.; Rand, C. L. J. Am. Chem. Soc. 1988, 110, 5383.
31. Kelly, T. R.; Schmidt, T. E.; Haggerty, J. C. Synthesis 1972, 544.
32. Carlsen, P. H.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
33. The authors have deposited atomic coordinates for this compound with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
34. Olah, G. A.; Vankar, Y. D.; Berrier, A. L. Synthesis 1980, 45 and references therein.
35. Blaszczak, L. C. U.S. Patent No. 4,771,135, 1988.
36. Deeter, J. B.; Hall, D. A.; Jordan, C. L.; Justice, R. M.; Kinnick, M. D.; Morin, J. M., Jr.; Paschal, J. W.; Ternansky, R. J. Tetrahedron Lett. 1993, 34, 3051.
37. Hanack, M.; Collins, C. J.; Stutz, H.; Benjamin, B. M. J. Am. Chem. Soc. 1981, 103, 2356.
38. Brain, E. G.; Eglington, J.; Nayler, J. H. C.; Osborne N. F.; Southgate, R.; Tolliday, P. J. Chem. Soc., Perkin Trans. 1 1977, 2479.
39. Crowell, T. A.; Halliday, B. H.; McDonald, J. H., III; Indelicato, J. M.; Pasini, C. E.; Wu, E. C. Y. J. Med. Chem. 1989, 32, 2436.
40. Shinkai, I.; Liu, T.; Reamer, R.; Sletzinger, M. Synthesis 1980, 924.
41. 5 at atmospheric pressure. Other general experimental details have been described: Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.
42. 5 at atmospheric pressure. Other general experimental details have been described: Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.
43. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis. 1982, 85.
44. Hanack, M.; Collins, C. J.; Stutz, H.; Benjamin, B. M. J. Am. Chem. Soc. 1981, 103, 2356.
45. Earnest, I.; Gosteli, J.; Greengrass C. W.; Holick, W.; Jaackman, D. E.; Pfaendler, H. R.; Woodward, R. B. J. Am. Chem. Soc. 1978, 100, 8214.