Cycloadditions of cephalosporins. A comprehensive study of the reaction of cephalosporin triflates with olefins, acetylenes, and dienes to form [2 + 2] and [4 + 2] adducts

Journal of Organic Chemistry

Volumn 62, Issue 15, 1997, Pages 4998-5016

  Elliott, Richard L ^a   Nicholson, Neville H ^a   Peaker, Fiona E ^a   Takle, Andrew K ^a   Richardson, Christine M ^a   Tyler, John W ^a   White, Janet ^a   Pearson, Michael J ^a   Eggleston, Drake S ^b   Haltiwanger, R Curtis ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b Dept of Phys and Struct Chemistry ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKADIENE; ALKENE DERIVATIVE; CEPHALOSPORIN DERIVATIVE;

ARTICLE; DRUG POTENTIATION; DRUG STRUCTURE; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 8544241746     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970176s     Document Type: Article

References (47)

1. Dürekheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180.
2. Kukolja, S.; Chauvette R. R. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vol. 1, pp 93-198.
3. Bateson, J. H.; Burton, G.; Fell, S. C. M. Biorg. Med. Chem. Lett. 1993, 3, 2219.
4. Ishiguro, M.; Iwata, H.; Nakatsuka, T.; Tanaka, R.; Maeda, Y.; Nishihara, T.; Noguchi, T. J. Antibiot. 1988, 41, 1685.
5. Bateson, J. H.; Burton, G.; Fell, S. C. M.; Smulders H. C. J. Antibiot. 1994, 47, 253.
6. Farina, V.; Kant, J. Synlett 1994, 565, and references cited therein.
7. Farina, V.; Baker, S. R.; Hauck, S. I. J. Org. Chem. 1989, 54, 4962.
8. Kant, J. J. Org. Chem. 1993, 58, 2296.
9. Sawyer, J. S.; Kucerovy, A.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1988, 110, 842.
10. Bateson, J. H.; Burton, G.; Elsmere, S. A.; Elliott, R. L. Synlett 1994, 152.
11. Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. For a Heck reaction on carbapenems, see: Nishi, K.; Narukawa, Y.; Onoue, H. Tetrahedron Lett. 1996, 37, 2987.
12. Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. For a Heck reaction on carbapenems, see: Nishi, K.; Narukawa, Y.; Onoue, H. Tetrahedron Lett. 1996, 37, 2987.
13. Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. For a Heck reaction on carbapenems, see: Nishi, K.; Narukawa, Y.; Onoue, H. Tetrahedron Lett. 1996, 37, 2987.
14. Conventional cephalsporin numbering has been used when referring to the bicyclic cephalosporin nucleus (see compound 4b), and systematic nomenclature has been used for the cycloadducts (see compounds 15, 19, and 95). α-Substituents are projected into the page while β-substituents are oriented out of the page.
15. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
16. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
17. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
18. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
19. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
20. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
21. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
22. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
23. Elliott, R. L.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1993, 58, 6954. Elliott, R. L.; Nicholson, N. H.; Peaker, F. E.; Takle, A. K.; Tyler, J. W.; White, J. J. Org. Chem. 1994, 59, 1606. Burton, G.; Elliott, R. L. (SmithKline Beecham plc) PCT Pat. Appl. WO 9318044, 16 Sept 1993; Chem. Abstr. 1994, 121, 57222. Burton, G.; Bateson, J. H.; Elliott, R. L.; Fell, S. C. M. (SmithKline Beecham plc) PCT Pat. Appl. WO 9400457, 6 Jan 1994; Chem. Abstr. 1994, 120, 191424. Elliott, R. L.; Nicholson, N. H.; Takle, A. K. (SmithKline Beecham plc) PCT Pat. Appl. WO 9421633, 29 Sept 1994; Chem. Abstr. 1995, 122, 31202. For other examples of polycyclic β-lactams, see: Niu C.; Pettersson T.; Miller M. J. J. Org. Chem. 1996, 61, 1014 and references therein.
24. The author has deposited atomic coordinates for 62 and 86 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.
25. Harnos, S.; Tivakornpannarai, S.; Waali, E. E. Tetrahedron Lett. 1986, 27, 3701. Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939. Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473. Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532. Bottini, A. T.; Hilton, L. L.; Plott, J. Tetrahedron 1975, 31, 1997. Sütbeyaz, Y.; Ceylan, M.; Seçen, H. J. Chem. Res., Synop. 1993, 293. Jamart-Grégoire, B.; Mercier-Girardot, S.; Ianelli, S.; Nardelli, M.; Caubère, P. Tetrahedron 1995, 51, 1973.
26. Harnos, S.; Tivakornpannarai, S.; Waali, E. E. Tetrahedron Lett. 1986, 27, 3701. Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939. Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473. Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532. Bottini, A. T.; Hilton, L. L.; Plott, J. Tetrahedron 1975, 31, 1997. Sütbeyaz, Y.; Ceylan, M.; Seçen, H. J. Chem. Res., Synop. 1993, 293. Jamart-Grégoire, B.; Mercier-Girardot, S.; Ianelli, S.; Nardelli, M.; Caubère, P. Tetrahedron 1995, 51, 1973.
27. Harnos, S.; Tivakornpannarai, S.; Waali, E. E. Tetrahedron Lett. 1986, 27, 3701. Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939. Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473. Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532. Bottini, A. T.; Hilton, L. L.; Plott, J. Tetrahedron 1975, 31, 1997. Sütbeyaz, Y.; Ceylan, M.; Seçen, H. J. Chem. Res., Synop. 1993, 293. Jamart-Grégoire, B.; Mercier-Girardot, S.; Ianelli, S.; Nardelli, M.; Caubère, P. Tetrahedron 1995, 51, 1973.
28. Harnos, S.; Tivakornpannarai, S.; Waali, E. E. Tetrahedron Lett. 1986, 27, 3701. Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939. Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473. Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532. Bottini, A. T.; Hilton, L. L.; Plott, J. Tetrahedron 1975, 31, 1997. Sütbeyaz, Y.; Ceylan, M.; Seçen, H. J. Chem. Res., Synop. 1993, 293. Jamart-Grégoire, B.; Mercier-Girardot, S.; Ianelli, S.; Nardelli, M.; Caubère, P. Tetrahedron 1995, 51, 1973.
29. Harnos, S.; Tivakornpannarai, S.; Waali, E. E. Tetrahedron Lett. 1986, 27, 3701. Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939. Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473. Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532. Bottini, A. T.; Hilton, L. L.; Plott, J. Tetrahedron 1975, 31, 1997. Sütbeyaz, Y.; Ceylan, M.; Seçen, H. J. Chem. Res., Synop. 1993, 293. Jamart-Grégoire, B.; Mercier-Girardot, S.; Ianelli, S.; Nardelli, M.; Caubère, P. Tetrahedron 1995, 51, 1973.
30. Harnos, S.; Tivakornpannarai, S.; Waali, E. E. Tetrahedron Lett. 1986, 27, 3701. Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939. Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473. Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532. Bottini, A. T.; Hilton, L. L.; Plott, J. Tetrahedron 1975, 31, 1997. Sütbeyaz, Y.; Ceylan, M.; Seçen, H. J. Chem. Res., Synop. 1993, 293. Jamart-Grégoire, B.; Mercier-Girardot, S.; Ianelli, S.; Nardelli, M.; Caubère, P. Tetrahedron 1995, 51, 1973.
31. Harnos, S.; Tivakornpannarai, S.; Waali, E. E. Tetrahedron Lett. 1986, 27, 3701. Christl, M.; Braun, M. Chem. Ber. 1989, 122, 1939. Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473. Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532. Bottini, A. T.; Hilton, L. L.; Plott, J. Tetrahedron 1975, 31, 1997. Sütbeyaz, Y.; Ceylan, M.; Seçen, H. J. Chem. Res., Synop. 1993, 293. Jamart-Grégoire, B.; Mercier-Girardot, S.; Ianelli, S.; Nardelli, M.; Caubère, P. Tetrahedron 1995, 51, 1973.
32. Newcomb, M. Tetrahedron 1993, 49, 1151. Newcomb, M.; Glenn, A. G. J. Am. Chem. Soc. 1989, 111, 275.
33. Newcomb, M. Tetrahedron 1993, 49, 1151. Newcomb, M.; Glenn, A. G. J. Am. Chem. Soc. 1989, 111, 275.
34. Hansch, C.; Leo A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
35. Ochiai, M.; Aki O.; Morimoto, A.; Okada, T. Tetrahedron Lett. 1972, 3241.
36. Crowell, T. A.; Hailiday, B. D.; McDonald J. H., III; Indelicato, J. M.; Pasini, C. E.; Wu, E. C. Y. J. Med. Chem. 1989, 32, 2436. Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3787. Bodurow, C.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081.
37. Crowell, T. A.; Hailiday, B. D.; McDonald J. H., III; Indelicato, J. M.; Pasini, C. E.; Wu, E. C. Y. J. Med. Chem. 1989, 32, 2436. Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3787. Bodurow, C.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081.
38. Crowell, T. A.; Hailiday, B. D.; McDonald J. H., III; Indelicato, J. M.; Pasini, C. E.; Wu, E. C. Y. J. Med. Chem. 1989, 32, 2436. Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3787. Bodurow, C.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081.
39. The rate difference between the chlorination of 3-hydroxycarbacephems and 3-hydroxycephems has been attributed to sulfur neighboring group participation. Burks, J. E., Jr.; Chelius, E. C.; Johnson, R. A. J. Org. Chem. 1994, 59, 5724.
40. Cainelli, G.; Contento, M.; Panunzio, M.; Sandri, S.; Umani-Ronchi, A.; Col, M. D. Synlett 1994, 243.
41. Tanaka, H.; Sumida, S.-i.; Torri, S. Tetrahedron Lett. 1996, 37, 5967.
42. Woodward, R. B.; Hoffman, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
43. SPARTAN Version 4.1, Wavefunction Inc., 18401 Von Karmen Avenue, No. 370, Irvine, CA 92715, 1995.
44. Kang, H-Y.; Lee, S. H.; Choi, K. I.; Koh, H. Y. Tetrahedron Lett. 1996, 37, 7549.
45. Tsunoda, T.; Hudlicky, T. Synlett 1990, 322.
46. Bordwell, F. G.; Lampert, B. B.; McKellin, W. H. J. Am. Chem. Soc. 1949, 71, 1702.
47. Dolbier, W. R., Jr.; Wicks, G. E. J. Am. Chem. Soc. 1985, 107, 3626.