Diastereoselective conjugate reduction and enolate trapping with glyoxylate imines. A concise approach to β-lactams that involves a ternary combination of components

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1693-1698

  Palomo, Claudio ^a   Aizpurua, Jesús Ma ^a   Gracenea, Jose Javier ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINONE DERIVATIVE; BETA LACTAM ANTIBIOTIC; GLYOXYLATE IMINE; GLYOXYLIC ACID DERIVATIVE; L 652117; L 680833; NIKKOMYCIN; UNCLASSIFIED DRUG;

CHEMICAL MODIFICATION; CONJUGATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NOTE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0039626613     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981574d     Document Type: Note

References (60)

1. For reviews on this subject, see: (a) Southgate, R.; Elson, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Tamm, C., Eds.; Springer: Vienna, 1985; Vol. 47, p 1.
2. (b) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer: Berlin, 1993; Vol. 2, p 621.
3. (c) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
4. (d) The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992.
5. For strategies on the synthesis of bicyclic β-lactams, see: (a) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ohno, M. Eds.; Springer: Berlin, 1990; Vol. 1, p 565.
6. (b) Kant, J.; Walker, D. G. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 121.
7. For reviews, see: (a) Edwards, P. D.; Bernstein, P. R. Med. Res. Rev. 1994, 14, 127.
8. (b) Mascaretti, O. A.; Boschetti, C. E.; Danelon, G. O.; Mata, E. G.; Roveri, O. A. Current Med. Chem. 1995, 1, 441.
9. Firestone, R. A.; Barker, P. L.; Pisano, J. M.; Ashe, B. M.; Dahlgren, M. E. Tetrahedron 1990, 46, 2255.
10. Shah, S. K.; Finke, P. E.; Brause, K. A.; Chandler, G. O.; Ashe, B. M.; Weston, H.; Maycock, A. L.; Mumford, R. A.; Doherty, J. B. Bioorg. Med. Chem. Lett. 1993, 3, 2295.
11. Kuo, D.; Weidner, J.; Griffin, P.; Shah, S. K.; Knight, W. B. Biochemistry 1994, 33, 8347.
12. For general reviews on β-lactam synthesis, see: (a) Koppel, G. A. In Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Vol. 42, p 219.
13. (b) Backes, J. In Houben-Weyl, Methoden der Organischen Chemie; Muller, E., Bayer, O., Eds.; Thieme: Stuttgart, 1991; Band E 16B, p 31.
14. (c) Dekimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; 1996; Vol. 1B, p 507. For recent reviews on asymmetric synthesis of β-lactams, see:
15. (d) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer: Berlin, 1990; Vol. 1, p 533.
16. (e) Ternansky, R. J.; Morin, J. M., Jr. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 257.
17. (f) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
18. For reviews, see: (a) Hart, D. J.; Ha, D. C. Chem. Rev. 1989, 89, 1447.
19. (b) Brown, M. J. Heterocycles 1989, 29, 2225.
20. (c) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A.-ur., Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431.
21. (d) Fujisawa, T.; Shimizu, M. Rev. Heteroatom. Chem. 1996, 15, 203.
22. (e) Cainelli, G.; Panunzio, M.; Giacomini, D.; Martelli, G.; Spunta, G.; Bandini, E. In Chemical Synthesis, Gnosis to Prognosis; Chatgilialoglu, C., Snieckus, V., Eds.; Kluwer Academic: Amsterdam, 1996; p 25.
23. (a) Yamamoto, Y.; Asao, N.; Uyehara, T. J. Am. Chem. Soc. 1992, 114, 5427.
24. (b) Asao, N.; Uyehara, T.; Tsukada, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 1995, 68, 2103.
25. (c) Davies, S. G.; Fenwick, D. R. J. Chem. Soc., Chem. Commun. 1997, 565.
26. For a comprehensive review on conjugate addition-enolate trapping, see: (d) Hulce, M.; Chapdelaine, M. J. In Comprehensive Organic Synthesis; Semmelhack, M. F., Ed.; Pergamon: Oxford, 1991; Vol. 4, p 237. For another approach to β-lactams involving a one-pot reaction of an amine, an aldehyde, and silyl ketene thioacetals, see:
27. (e) Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. J. Org. Chem. 1996, 61, 8293.
28. (a) Palomo, C.; Aizpurua, J. M.; Urchegui, R. J. Chem. Soc., Chem. Commun. 1990, 1390.
29. (b) Palomo, C.; Aizpurua, J. M.; Urchegui, R.; Iturburu, M. J. Org. Chem. 1992, 57, 1571.
30. For reviews on asymmetric conjugate additions, including conjugate reductions, see: (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
31. (b) Schmalz, H.-G. In Comprehensive Organic Synthesis; Semmelhack, M. F., Ed.; Pergamon: Oxford, 1991; Vol. 4, p 199.
32. (c) Leonard, J. Contemp. Org. Synth. 1994, 1, 387.
33. (d) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
34. Oppolzer, W.; Poli, G. Tetrahedron Lett. 1986, 27, 4717.
35. For conjugate reductions of enones and enoates with K-and L-Selectride, see: (a) Reference 12.
36. (b) Fortunato, J. M.; Ganem, B. J. Org. Chem. 1976, 41, 2194.
37. (c) Bell, R. A.; Turner, J. V. Tetrahedron Lett. 1981, 22, 4871.
38. (d) Cativiela, C.; Diaz-de-Villegas, D.; Galvez, J. A. Bull. Chem. Soc. Jpn. 1992, 65, 1657. For an extensive list of references concerning conjugate reductions, see:
39. (e) Kawakami, T.; Miyatake, M.; Shibata, I.; Baba, A. J. Org. Chem. 1996, 61, 376.
40. In general, glyoxylate imines do not react well with enolates, particularly with lithium enolates, to give β-lactams, see: Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 109, 1129.
41. Johnson, C. R.; Marren, T. J. Tetrahedron Lett. 1987, 28, 27.
42. 4-tert-Butoxycarbonyl-β-lactams 8a-c showed very deficient chromatographic peak resolution in comparison with β-lactams 9a-c, which were prepared in their racemic form by the ketene-imine [2 + 2] cycloaddition reaction of the corresponding alkanoyl chlorides with the imine derived from p-anisidine and methyl glyoxylate, according to our previously reported procedure: Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Ganboa, I., J. Chem. Soc., Chem. Commun. 1990, 248.
43. Cainelli, G.; Panunzio, M.; Giacomini, D.; Martelli, G.; Spunta, G. J. Am. Chem. Soc. 1988, 110, 6879. For a review on (+)-PS-5, see: Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; p 565.
44. Cainelli, G.; Panunzio, M.; Giacomini, D.; Martelli, G.; Spunta, G. J. Am. Chem. Soc. 1988, 110, 6879. For a review on (+)-PS-5, see: Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; p 565.
45. Adlington, R. M.; Baldwin, J. E.; Chen, B.; Cooper, S. L.; McCoull, W.; Pritchard, G. J.; Howe, T. J.; Becker, G. W.; Hermann, R. B.; McNulty, A. M.; Neubauer, B. L. Bioorg. Med. Chem. Lett. 1997, 7, 1689.
46. Palomo, C.; Aizpurua, J. M.; Ontoria, J. M.; Iturburu, M. Tetrahedron Lett. 1992, 33, 4823. For a recent review on β-lactams as building blocks of β-amino acids and their derivatives, see: Palomo, C.; Aizpurua, J. M.; Ganboa, I. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997, p 279.
47. Palomo, C.; Aizpurua, J. M.; Ontoria, J. M.; Iturburu, M. Tetrahedron Lett. 1992, 33, 4823. For a recent review on β-lactams as building blocks of β-amino acids and their derivatives, see: Palomo, C.; Aizpurua, J. M.; Ganboa, I. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997, p 279.
48. For some recent examples on synthesis of the N-terminal amino acid of nikkomycins, see: (a) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1991, 56, 4875.
49. (b) Barluenga, J.; Viado, A. L.; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem. 1993, 58, 5972.
50. (c) Mukai, C.; Miyakawa, M.; Hanaoka, M. Synlett 1994, 165.
51. (d) Akita, H.; Chen, C. Y.; Uchida, K. Tetrahedron: Asymmetry 1995, 6, 2131.
52. (e) Mandville, G.; Ahmar, M.; Bloch, R. J. Org. Chem. 1996, 61, 1122.
53. (f) Aggarwal, V. K.; Monteiro, N.; Tarver, G. J.; Lindell, S. D. J. Org. Chem. 1996, 61, 1192.
54. (g) Tamura, O.; Mita, N.; Kusaka, N.; Suzuki, H.; Sakamoto, M. Tetrahedron Lett. 1997, 38, 429.
55. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
56. Palomo, C.; Aizpurua, J. M.; García, J. M.; Iturburu, M. Odriozola, J. M. J. Org. Chem. 1994, 59, 5184.
57. Another paper will deal with conjugate additions of carbon nucleophiles and enolate trapping with glyoxylate imines, see: Palomo, C.: Aizpurua, J. M.; Gracenea, J. J.; Garcia-Granda, S.; Pertierra, P. Eur. J. Org. Chem. 1998, 2201, 1.
58. Lee, J. Y.; Chung, J.; Kim, B. H. Synlett 1994, 197.
59. Oppolzer, W.; Chapuis, C.; Bernardelli, G. Helv. Chim. Acta 1984, 67, 1397.
60. Cossio, F. P.; Lopez, M. C.; Palomo, C. Tetrahedron 1987, 43, 3963.