Aldehydes and ketones as dipolarophiles: Application to the synthesis of oxapenams

Chemical Communications

Volumn , Issue 3, 1999, Pages 249-250

  Andrews, Mark D ^a   Brown, Giles A ^a   Charmant, Jonathan P H ^a   Peakman, Torren M ^a   Rebello, Arlene ^a   Walsh, Kenneth E ^a   Gallagher, Timothy ^a   Hales, Neil J ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BETA LACTAM; BETA LACTAMASE INHIBITOR; CARBON; HEXAFLUOROACETONE; KETONE; OXAPENAM; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; HEAT; LYSIS;

EID: 0033531361     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808688e     Document Type: Article

References (37)

1. R. D. G. Cooper, in Topics in Antibiotic Chemistry, ed. P. G. Sammes, Ellis Horwood Ltd., Chichester, 1980, vol. 3, p. 39; W. Dürckheimer, J. Blumbach, R. Lattrell and K. H. Scheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; Recent Advances in the Chemistry and Biology of β-Lactams and β-Lactam Antibiotics, ed. G. I. Georg, Bioorg. Med. Chem. Lett. (Symposia-in-print No 8), 1993, 3, 2159.
2. R. D. G. Cooper, in Topics in Antibiotic Chemistry, ed. P. G. Sammes, Ellis Horwood Ltd., Chichester, 1980, vol. 3, p. 39; W. Dürckheimer, J. Blumbach, R. Lattrell and K. H. Scheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; Recent Advances in the Chemistry and Biology of β-Lactams and β-Lactam Antibiotics, ed. G. I. Georg, Bioorg. Med. Chem. Lett. (Symposia-in-print No 8), 1993, 3, 2159.
3. R. D. G. Cooper, in Topics in Antibiotic Chemistry, ed. P. G. Sammes, Ellis Horwood Ltd., Chichester, 1980, vol. 3, p. 39; W. Dürckheimer, J. Blumbach, R. Lattrell and K. H. Scheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180; Recent Advances in the Chemistry and Biology of β-Lactams and β-Lactam Antibiotics, ed. G. I. Georg, Bioorg. Med. Chem. Lett. (Symposia-in-print No 8), 1993, 3, 2159.
4. T. T. Howarth, A. G. Brown and T. J. King, J. Chem. Soc., Chem. Commun., 1976, 266; D. Brown, J. R. Evans and R. A. Fletton, J. Chem. Soc., Chem. Commun., 1979, 282. The latter authors coined the term 'clavam'.
5. T. T. Howarth, A. G. Brown and T. J. King, J. Chem. Soc., Chem. Commun., 1976, 266; D. Brown, J. R. Evans and R. A. Fletton, J. Chem. Soc., Chem. Commun., 1979, 282. The latter authors coined the term 'clavam'.
6. (a) M. Wanning, H. Zähner, B. Krone and A. Zeeck, Tetrahedron Lett., 1981, 22, 2539;
7. (b) D. L. Pruess and M. Kellett, J. Antibiot., 1983, 36, 208;
8. (c) J. E. Baldwin, R. M. Adlington, J. S. Bryans, A. O. Bringhen, J. B. Coates, N. P. Crouch, M. D. Lloyd, C. J. Schofield, S. W. Elson, K. H. Baggaley, R. Cassels and N. Nicholson, Tetrahedron, 1991, 47, 4089.
9. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
10. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
11. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
12. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
13. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
14. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
15. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
16. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
17. W.Nagata, Pure Appl. Chem., 1989, 61, 325; M. Murakami, T. Aoki, M. Matsuura and W. Nagata, J. Antibiot., 1990, 43, 1441; H. R. Pfaendler, W. Hendel and U. Nagel, Z. Naturforsch. Teil B., 1992, 47, 1037; H. Wild and W. Hartwig, Synthesis, 1992, 1099; H. Wild, Tetrahedron Lett., 1993, 34, 285; H. R. Pfaendler, F. Weisner and K. Metzger, Bioorg. Med. Chem. Lett., 1993, 3, 2211; M. Botta, M. Crucianelli, R. Saladino, C. Mozzetti and R. Nicoletti, Tetrahedron, 1996, 52, 10205; H. R. Pfaendler and C. Medicus, Bioorg. Med. Chem. Lett., 1997, 7, 623; P. Couture and J. Warkentin, Can. J. Chem., 1998, 76, 241.
18. J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Chem. Commun., 1980, 49; G. H. Hakimelahi and G. Just, Can. J. Chem., 1981, 59, 941; J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Perkin Trans. 1, 1983, 649; D. Häbich, P. Naab and K. Metzger, Tetrahedron Lett., 1983, 24, 2559; B. H. Lee, A. Biswas and M. J. Miller, J. Org. Chem., 1986, 51, 106.
19. J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Chem. Commun., 1980, 49; G. H. Hakimelahi and G. Just, Can. J. Chem., 1981, 59, 941; J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Perkin Trans. 1, 1983, 649; D. Häbich, P. Naab and K. Metzger, Tetrahedron Lett., 1983, 24, 2559; B. H. Lee, A. Biswas and M. J. Miller, J. Org. Chem., 1986, 51, 106.
20. J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Chem. Commun., 1980, 49; G. H. Hakimelahi and G. Just, Can. J. Chem., 1981, 59, 941; J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Perkin Trans. 1, 1983, 649; D. Häbich, P. Naab and K. Metzger, Tetrahedron Lett., 1983, 24, 2559; B. H. Lee, A. Biswas and M. J. Miller, J. Org. Chem., 1986, 51, 106.
21. J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Chem. Commun., 1980, 49; G. H. Hakimelahi and G. Just, Can. J. Chem., 1981, 59, 941; J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Perkin Trans. 1, 1983, 649; D. Häbich, P. Naab and K. Metzger, Tetrahedron Lett., 1983, 24, 2559; B. H. Lee, A. Biswas and M. J. Miller, J. Org. Chem., 1986, 51, 106.
22. J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Chem. Commun., 1980, 49; G. H. Hakimelahi and G. Just, Can. J. Chem., 1981, 59, 941; J. Brennan, G. Richardson and R. J. Stoodley, J. Chem. Soc., Perkin Trans. 1, 1983, 649; D. Häbich, P. Naab and K. Metzger, Tetrahedron Lett., 1983, 24, 2559; B. H. Lee, A. Biswas and M. J. Miller, J. Org. Chem., 1986, 51, 106.
23. Synthetic routes to oxapenams: (a) S. Oida, A. Yoshida and E. Ohki, Chem. Pharm. Bull., 1978, 26, 448;
24. (b) T. Kobayashi, Y. Iwano and K. Hirai, Chem. Pharm. Bull., 1978, 26, 1761;
25. (c) P. H. Bentley and E. Hunt, J. Chem. Soc., Perkin Trans. 1, 1980, 2222;
26. (d) J. C. Müller, V. Toome, D. L. Pruess, J. F. Blount and M. Weigele, J. Antibiot., 1983, 36, 217;
27. (e) A. G. Brown, D. F. Corbett, J. Goodacre, J. B. Harbridge, T. T. Howarth, R. J. Ponsford, I. Stirling and T. J. King, J. Chem. Soc., Perkin Trans. 1, 1984, 635;
28. (f) S. De Bernardo, J. P. Tengi, G. J. Sasso and M. Weigele, J. Org. Chem., 1985, 50, 3457;
29. (g) D. Hoppe and T. Hilpert, Tetrahedron, 1987, 43, 2467;
30. (h) B. Furman, Z. Kaluza and M. Chmielewski, J. Org. Chem., 1997, 62, 3135;
31. (i) O. Neuss, B. Furman, Z. Kaluza and M. Chmielewski, Heterocycles, 1997, 45, 265.
32. O. Tsuge and S. Kanemasa, Advanced Heterocyclic Chemistry, ed. A. R. Katritzky, Academic Press, San Diego, 1989, vol. 45, p. 231.
33. (a) S. R. Martel, R. Wisedale, T. Gallagher, L. D. Hall, M. F. Mahon, R. H. Bradbury and N. J. Hales, J. Am. Chem. Soc., 1997, 119, 2309;
34. (b) D. Planchenault, R. Wisedale, T. Gallagher and N. J. Hales, J. Org. Chem., 1997, 62, 3438;
35. (c) S. R. Martel, D. Planchenault, R. Wisedale, T. Gallagher and N. J. Hales, Chem. Commun., 1997, 1987.
36. B. Furman, P. Krajewski, Z. Urbanczyk-Lipkowska, J. Frelek, Z. Kaluza, L. Kozerski and M. Chmielewski, J. Chem. Soc., Perkin Trans. 2, 1998, 1737.
37. D. A. Fletcher, R. F. McMeeking and D. J. Parkin, J. Chem. Inf. Comput. Sci., 1996, 36, 746.