A direct and convergent approach to penams and penems

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3438-3439

  Planchenault, Denis ^a   Wisedale, Richard ^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

PENAM DERIVATIVE; PENEM DERIVATIVE; THIACLAVAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030914479     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962367l     Document Type: Article

References (37)

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2. Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., German, M., Eds.; Academic Press: New York, 1982; Vols. 1-3. Dürchheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180. Recent Advances in the Chemistry and Biology of β-Lactams and β-Lactam Antibiotics; Georg, G. I., Ed.; VCH: New York, 1993.
3. Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., German, M., Eds.; Academic Press: New York, 1982; Vols. 1-3. Dürchheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180. Recent Advances in the Chemistry and Biology of β-Lactams and β-Lactam Antibiotics; Georg, G. I., Ed.; VCH: New York, 1993.
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8. Recent work in this area of β-lactam chemistry has been presented: Bioorg. Med. Chem. Lett. (Symposia-in-Print No. 8) 1993, 3, 2159-2313. The penam numbering scheme, see 1, is used throughout this paper.
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12. Oxazolidinone 4 is most readily obtained from clavulanic acid, a component of Augmentin (SB Pharmaceuticals): (a) Brown, A. G.; Corbett, D. F.; Goodacre, J.; Harbidge, J. B.; Howarth, T. T.; Ponsford, R. J.; Stirling, I.; King, T. J. J. Chem. Soc., Perkin Trans. 1 1984, 635. (b) Howarth, T. T.; Stirling, I. Ger. Offen. 2,655,675; Chem. Abstr. 1977, 87, 102 313. For other approaches to the synthesis of oxazolidinone 4 see: Bentley, P. H.; Berry, P. D.; Brooks, G.; Gilpin, M. L.; Hunt, E.; Zomaya, I. I. J. Chem. Soc., Chem. Commun. 1977, 748. Campbell, M. M.; Jasys, V. J. Heterocycles 1981, 16, 1487.
13. Oxazolidinone 4 is most readily obtained from clavulanic acid, a component of Augmentin (SB Pharmaceuticals): (a) Brown, A. G.; Corbett, D. F.; Goodacre, J.; Harbidge, J. B.; Howarth, T. T.; Ponsford, R. J.; Stirling, I.; King, T. J. J. Chem. Soc., Perkin Trans. 1 1984, 635. (b) Howarth, T. T.; Stirling, I. Ger. Offen. 2,655,675; Chem. Abstr. 1977, 87, 102 313. For other approaches to the synthesis of oxazolidinone 4 see: Bentley, P. H.; Berry, P. D.; Brooks, G.; Gilpin, M. L.; Hunt, E.; Zomaya, I. I. J. Chem. Soc., Chem. Commun. 1977, 748. Campbell, M. M.; Jasys, V. J. Heterocycles 1981, 16, 1487.
14. Oxazolidinone 4 is most readily obtained from clavulanic acid, a component of Augmentin (SB Pharmaceuticals): (a) Brown, A. G.; Corbett, D. F.; Goodacre, J.; Harbidge, J. B.; Howarth, T. T.; Ponsford, R. J.; Stirling, I.; King, T. J. J. Chem. Soc., Perkin Trans. 1 1984, 635. (b) Howarth, T. T.; Stirling, I. Ger. Offen. 2,655,675; Chem. Abstr. 1977, 87, 102 313. For other approaches to the synthesis of oxazolidinone 4 see: Bentley, P. H.; Berry, P. D.; Brooks, G.; Gilpin, M. L.; Hunt, E.; Zomaya, I. I. J. Chem. Soc., Chem. Commun. 1977, 748. Campbell, M. M.; Jasys, V. J. Heterocycles 1981, 16, 1487.
15. Oxazolidinone 4 is most readily obtained from clavulanic acid, a component of Augmentin (SB Pharmaceuticals): (a) Brown, A. G.; Corbett, D. F.; Goodacre, J.; Harbidge, J. B.; Howarth, T. T.; Ponsford, R. J.; Stirling, I.; King, T. J. J. Chem. Soc., Perkin Trans. 1 1984, 635. (b) Howarth, T. T.; Stirling, I. Ger. Offen. 2,655,675; Chem. Abstr. 1977, 87, 102 313. For other approaches to the synthesis of oxazolidinone 4 see: Bentley, P. H.; Berry, P. D.; Brooks, G.; Gilpin, M. L.; Hunt, E.; Zomaya, I. I. J. Chem. Soc., Chem. Commun. 1977, 748. Campbell, M. M.; Jasys, V. J. Heterocycles 1981, 16, 1487.
16. Oxazolidinone 4 is most readily obtained from clavulanic acid, a component of Augmentin (SB Pharmaceuticals): (a) Brown, A. G.; Corbett, D. F.; Goodacre, J.; Harbidge, J. B.; Howarth, T. T.; Ponsford, R. J.; Stirling, I.; King, T. J. J. Chem. Soc., Perkin Trans. 1 1984, 635. (b) Howarth, T. T.; Stirling, I. Ger. Offen. 2,655,675; Chem. Abstr. 1977, 87, 102 313. For other approaches to the synthesis of oxazolidinone 4 see: Bentley, P. H.; Berry, P. D.; Brooks, G.; Gilpin, M. L.; Hunt, E.; Zomaya, I. I. J. Chem. Soc., Chem. Commun. 1977, 748. Campbell, M. M.; Jasys, V. J. Heterocycles 1981, 16, 1487.
17. For the application of azomethine ylide reactivity to the synthesis of carbapenams and carbapenems, see: Martel, S. R.; Wisedale, R.; Gallagher, T.; Hall, L. D.; Mahon, M. F.; Bradbury, R. H.; Hales, N. J. J. Am. Chem. Soc. 1997, 119, 2309. While the precise nature of the 1,3-dipolar species involved in Scheme 1 has not been determined azomethine ylide 5 offers a convenient way to rationalize the products available.
18. The relative (and thermodynamically more stable) configuration between C(3) and C(5) of adducts 6a,b, 7a-d, and 11 (penicillin stereochemistry) is based on chemical shift comparisons to those observed in the diastereomeric series and on the absence of a long-range coupling (1-1.5 Hz) between H(3) and H(6β). Smale, T. C.; Southgate, R. J. Chem. Soc., Perkin Trans. 1 1985, 2235. Wolfe, S.; Sterzycki, R. Z. Can. J. Chem. 1987, 65, 26. Barrett, A. G. M.; Sakadarat, S. J. Org. Chem. 1990, 55, 5110.
19. The relative (and thermodynamically more stable) configuration between C(3) and C(5) of adducts 6a,b, 7a-d, and 11 (penicillin stereochemistry) is based on chemical shift comparisons to those observed in the diastereomeric series and on the absence of a long-range coupling (1-1.5 Hz) between H(3) and H(6β). Smale, T. C.; Southgate, R. J. Chem. Soc., Perkin Trans. 1 1985, 2235. Wolfe, S.; Sterzycki, R. Z. Can. J. Chem. 1987, 65, 26. Barrett, A. G. M.; Sakadarat, S. J. Org. Chem. 1990, 55, 5110.
20. The relative (and thermodynamically more stable) configuration between C(3) and C(5) of adducts 6a,b, 7a-d, and 11 (penicillin stereochemistry) is based on chemical shift comparisons to those observed in the diastereomeric series and on the absence of a long-range coupling (1-1.5 Hz) between H(3) and H(6β). Smale, T. C.; Southgate, R. J. Chem. Soc., Perkin Trans. 1 1985, 2235. Wolfe, S.; Sterzycki, R. Z. Can. J. Chem. 1987, 65, 26. Barrett, A. G. M.; Sakadarat, S. J. Org. Chem. 1990, 55, 5110.
21. (a) Oida, S.; Yoshida, A.; Hayashi, T.; Takeda, N.; Ohki, E. Chem. Pharm. Bull. 1980, 28, 3232.
22. (b) Oida, S.; Yoshida, A.; Hayashi, T.; Nakayama, E.; Sato, S.; Ohki, E. Tetrahedron Lett. 1980, 619.
23. (a) Beels, C. M. D.; Abu-Rabie, M. S.; Murray-Rust, P.; Murray-Rust, J. J. Chem. Soc., Chem. Commun. 1979, 665.
24. (b) Henderson, A.; Johnson, G.; Moore, K. W.; Ross, B. C. J. Chem. Soc., Chem. Commun. 1982, 809.
25. (c) Yoshida, A.; Hayashi, T.; Takeda, N.; Oida, S.; Ohki, E. Chem. Pharm. Bull. 1983, 31, 768.
26. Cherry, P. C.; Newall, C. E.; Watson, N. S. J. Chem. Soc., Chem. Commun. 1979, 663.
27. For alternative syntheses of thiaclavams (exocyclic penems), see: (a) Cherry, P. C.; Evans, D. N.; Watson, N. S.; Murray-Rust, P.; Murray-Rust, J. Tetrahedron Lett. 1980, 561. (b) Baldwin, J. E.; Forrest, A. K.; Ko, S.; Sheppard, L. N. J. Chem. Soc., Chem. Commun. 1987, 81. (c) Tanaka, H.; Kameyama, Y.; Kosaka, A.; Yamauchi, T.; Torii, S. Tetrahedron Lett. 1991, 32, 7445. (d) Tanaka, H.; Kameyama, Y.; Yamauchi, T.; Torii, S. J. Chem. Soc., Chem. Commun. 1992, 1793. (e) Tanaka, H.; Sumida, S.; Sorajo, K.; Torii, S. J. Chem. Soc., Chem. Commun. 1994, 1461.
28. For alternative syntheses of thiaclavams (exocyclic penems), see: (a) Cherry, P. C.; Evans, D. N.; Watson, N. S.; Murray-Rust, P.; Murray-Rust, J. Tetrahedron Lett. 1980, 561. (b) Baldwin, J. E.; Forrest, A. K.; Ko, S.; Sheppard, L. N. J. Chem. Soc., Chem. Commun. 1987, 81. (c) Tanaka, H.; Kameyama, Y.; Kosaka, A.; Yamauchi, T.; Torii, S. Tetrahedron Lett. 1991, 32, 7445. (d) Tanaka, H.; Kameyama, Y.; Yamauchi, T.; Torii, S. J. Chem. Soc., Chem. Commun. 1992, 1793. (e) Tanaka, H.; Sumida, S.; Sorajo, K.; Torii, S. J. Chem. Soc., Chem. Commun. 1994, 1461.
29. For alternative syntheses of thiaclavams (exocyclic penems), see: (a) Cherry, P. C.; Evans, D. N.; Watson, N. S.; Murray-Rust, P.; Murray-Rust, J. Tetrahedron Lett. 1980, 561. (b) Baldwin, J. E.; Forrest, A. K.; Ko, S.; Sheppard, L. N. J. Chem. Soc., Chem. Commun. 1987, 81. (c) Tanaka, H.; Kameyama, Y.; Kosaka, A.; Yamauchi, T.; Torii, S. Tetrahedron Lett. 1991, 32, 7445. (d) Tanaka, H.; Kameyama, Y.; Yamauchi, T.; Torii, S. J. Chem. Soc., Chem. Commun. 1992, 1793. (e) Tanaka, H.; Sumida, S.; Sorajo, K.; Torii, S. J. Chem. Soc., Chem. Commun. 1994, 1461.
30. For alternative syntheses of thiaclavams (exocyclic penems), see: (a) Cherry, P. C.; Evans, D. N.; Watson, N. S.; Murray-Rust, P.; Murray-Rust, J. Tetrahedron Lett. 1980, 561. (b) Baldwin, J. E.; Forrest, A. K.; Ko, S.; Sheppard, L. N. J. Chem. Soc., Chem. Commun. 1987, 81. (c) Tanaka, H.; Kameyama, Y.; Kosaka, A.; Yamauchi, T.; Torii, S. Tetrahedron Lett. 1991, 32, 7445. (d) Tanaka, H.; Kameyama, Y.; Yamauchi, T.; Torii, S. J. Chem. Soc., Chem. Commun. 1992, 1793. (e) Tanaka, H.; Sumida, S.; Sorajo, K.; Torii, S. J. Chem. Soc., Chem. Commun. 1994, 1461.
31. For alternative syntheses of thiaclavams (exocyclic penems), see: (a) Cherry, P. C.; Evans, D. N.; Watson, N. S.; Murray-Rust, P.; Murray-Rust, J. Tetrahedron Lett. 1980, 561. (b) Baldwin, J. E.; Forrest, A. K.; Ko, S.; Sheppard, L. N. J. Chem. Soc., Chem. Commun. 1987, 81. (c) Tanaka, H.; Kameyama, Y.; Kosaka, A.; Yamauchi, T.; Torii, S. Tetrahedron Lett. 1991, 32, 7445. (d) Tanaka, H.; Kameyama, Y.; Yamauchi, T.; Torii, S. J. Chem. Soc., Chem. Commun. 1992, 1793. (e) Tanaka, H.; Sumida, S.; Sorajo, K.; Torii, S. J. Chem. Soc., Chem. Commun. 1994, 1461.
32. Isomerization of penems to thiaclavams and structural assignment: Douglas, J. L.; Martel, A.; Caron, G.; Ménard, M.; Silveira, L.; Clardy, J. Can. J. Chem. 1984, 62, 2282. See also ref 11b.
33. In reactions of 7a-d, no evidence for oxidation of the endocyclic sulfur atom, which is presumably less reactive for both steric and electronic reasons, has been detected. For relatived observations: Hanessian, S.; Bedeschi, A.; Battistini, C.; Mongelli, N. J. Am. Chem. Soc. 1985, 107, 1438. Fahey, J. L.; Lange, B. C.; Van der Veen, J. M.; Young, G. R.; Bose, A. K. J. Chem. Soc., Perkin Trans. 1 1977, 1117. Chemoselective oxidation of 2-thio-substituted penems has also been reported: Girijavallabhan, V. M.; McCombie, S. W.; Pinto, P.; Lin, S.-I.; Versace, R. J. Chem. Soc., Chem. Commun. 1987, 691. Krahmwer-Seifert, U.; Emmer, G. Heterocycles 1984, 22, 375.
34. In reactions of 7a-d, no evidence for oxidation of the endocyclic sulfur atom, which is presumably less reactive for both steric and electronic reasons, has been detected. For relatived observations: Hanessian, S.; Bedeschi, A.; Battistini, C.; Mongelli, N. J. Am. Chem. Soc. 1985, 107, 1438. Fahey, J. L.; Lange, B. C.; Van der Veen, J. M.; Young, G. R.; Bose, A. K. J. Chem. Soc., Perkin Trans. 1 1977, 1117. Chemoselective oxidation of 2-thio-substituted penems has also been reported: Girijavallabhan, V. M.; McCombie, S. W.; Pinto, P.; Lin, S.-I.; Versace, R. J. Chem. Soc., Chem. Commun. 1987, 691. Krahmwer-Seifert, U.; Emmer, G. Heterocycles 1984, 22, 375.
35. In reactions of 7a-d, no evidence for oxidation of the endocyclic sulfur atom, which is presumably less reactive for both steric and electronic reasons, has been detected. For relatived observations: Hanessian, S.; Bedeschi, A.; Battistini, C.; Mongelli, N. J. Am. Chem. Soc. 1985, 107, 1438. Fahey, J. L.; Lange, B. C.; Van der Veen, J. M.; Young, G. R.; Bose, A. K. J. Chem. Soc., Perkin Trans. 1 1977, 1117. Chemoselective oxidation of 2-thio-substituted penems has also been reported: Girijavallabhan, V. M.; McCombie, S. W.; Pinto, P.; Lin, S.-I.; Versace, R. J. Chem. Soc., Chem. Commun. 1987, 691. Krahmwer-Seifert, U.; Emmer, G. Heterocycles 1984, 22, 375.
36. In reactions of 7a-d, no evidence for oxidation of the endocyclic sulfur atom, which is presumably less reactive for both steric and electronic reasons, has been detected. For relatived observations: Hanessian, S.; Bedeschi, A.; Battistini, C.; Mongelli, N. J. Am. Chem. Soc. 1985, 107, 1438. Fahey, J. L.; Lange, B. C.; Van der Veen, J. M.; Young, G. R.; Bose, A. K. J. Chem. Soc., Perkin Trans. 1 1977, 1117. Chemoselective oxidation of 2-thio-substituted penems has also been reported: Girijavallabhan, V. M.; McCombie, S. W.; Pinto, P.; Lin, S.-I.; Versace, R. J. Chem. Soc., Chem. Commun. 1987, 691. Krahmwer-Seifert, U.; Emmer, G. Heterocycles 1984, 22, 375.
37. 11 Assignment of (Z)-geometry of 9d is based on NOE experiments involving the alkenyl proton and H(3) and isomerization of 9d to the endo isomer 8d took place under basic conditions. However, this is a slower and less efficient reaction than was observed for the formation of 8c from 9c.