Palladium-promoted derivatization of novel C-fused penem ring systems

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8647-8650

  Konaklieva, Monika I ^a   Shi, Hongchang ^a   Turos, Edward ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PENEM DERIVATIVE;

ARTICLE; CATALYSIS; DERIVATIZATION; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030786788     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10376-8     Document Type: Article

References (45)

1. (a) Travis, J.; Culott, E.; Nowak, R. Science 1994, 264, 359.
2. (b) Spratt, B.G., ibid., 1994, 264, 388.
3. (c) Antimicrobial Drug Resistance Bryan, L.E., Ed., Academic Press: New York, 1984.
4. (d) Gunda, E.T.; Jaszberenyi, J.C. Prog. Med. Chem. 1977, 14, 181.
5. For discussions and lead references, refer to: The Chemistry of β-Lactams; Page, M.I., Ed., Blackie Academic and Professional: New York, 1996, pp. 255-257 and pp. 306-321 as well as the following articles:
6. (a) Nangia, A.; Chandrakala, P.S. Tetrahedron Lett. 1995, 36, 7771.
7. (b) Singh, R.; Cooper, R.D.G. Tetrahedron 1994, 50, 12049.
8. (c) Marchand-Brynaert, J.; Vanlierde, H.; Ghosez, L. Bull. Soc. Chim. Belg. 1988, 97, 1081.
9. (d) Taylor, E.C.; Hinkle, J.S. J. Org. Chem. 1987, 52, 4107 and references cited therein,
10. (e) Jungheim, L.N.; Sigmund, S.K. J. Org. Chem. 1987, 52, 4007 and references cited,
11. (f) Baldwin, J.E.; Adlington, R.M.; Jones, R.H.; Schofield, C.J.; Zaracostas, C. Tetrahedron 1986, 42, 4879.
12. (g) Tymiak, A.A.; Culver, C.A.; Malley, M.F.; Gougoutas, J.Z. J. Org. Chem. 1985, 50, 5491.
13. (a) Ren, X.-F.; Konaklieva, M.I.; Turos, E. J. Org. Chem. 1995, 60, 4980.
14. (b) Ren, X.-F.; Turos, E. J. Org. Chem. 1994, 59, 5858.
15. (a) Franceschi, G.; Alpegiani, M; Battistini, C.; Bedeschi, A.; Perrone, E.; Zarini, F. Pure & Appl. Chem. 1987, 59, 467.
16. (b) Pfaendler, H.R.; Gosteli, J.; Woodward, R.B. J. Am. Chem. Soc. 1980, 702, 2039.
17. (c) Lang, M.; Prasad, K.; Hulick, W.; Gosteli, J.; Ernest, I.; Woodward, R.B. J. Am. Chem. Soc. 1979, 101, 6296.
18. (d) Ernest, I.; Gosteli, J.; Woodward, R.B. J. Am. Chem. Soc. 1979, 101, 6301.
19. (e) Pfaendler, H.R.; Gosteli, J.; Woodward, R.B. J. Am. Chem. Soc. 1979, 101, 6306.
20. (f) Ernest, I.; Gosteli, J.; Greengrass, C.W.; Holick, W.; Jackman, D.E.; Pfaendler, H.R.; Woodward, R.B. J. Am. Chem. Soc. 1978, 100, 8214.
21. (a) Farina, V.; Baker, S.R.; Benigni, D.A.; Hauck, S.I.; Sapino, C. J. Org. Chem. 1990, 55, 5833.
22. (b) McKean, D.R.; Parrinello, G.; Renaldo, A.F.; Stille, J.K. J. Org. Chem. 1987, 52, 422.
23. (c) Stille, J.K.; Groh, B.L. J. Am. Chem. Soc. 1987, 709, 813.
24. (d) Stille, J.K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
25. (e) Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033.
26. (a) Grigg, R.; Sridharan, V.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1139.
27. (b) Schoenberg, A.; Bartoletti, I.; Heck, R.F. J. Org. Chem. 1974, 39, 3318.
28. For examples of palladium-catalyzed reactions on beta-lactam ring systems, see (a) Barrett, D.; Terasawa, T.; Okuda, S.; Kawabata, K.; Yasuda, N.; Kamimura, T.; Sakane, K.; Takaya, T. J. Antibiotics 1997, 50, 100.
29. (b) Armitage, M.A.; Lathbury, D.C.; Sweeney, J.B. Tetrahedron Lett. 1995, 36, 775.
30. (c) Burwood, M.; Davies, B.; Diaz, I.; Grigg, R,; Molina, P.; Sridharan, V.; Hughes, M. Tetrahedron Lett. 1995, 36, 9053.
31. (d) Rano, T.A.; Greenlee, M.L.; DiNinno, P.P. Tetrahedron Lett. 1990, 31, 2853.
32. (e) Cook, G.K.; Hornback, W.J.; Jordan, C.L.; McDonald, J.H.; Munroe, J.E. J. Org. Chem. 1989, 54, 5828.
33. (f) Farina, V.; Baker, S.R.; Hauck, S.I. J. Org. Chem. 1989, 54, 4962.
34. (g) Farina, V.; Baker, S.R.; Benigni, D.A.; Sapino, C. Tetrahedron Lett. 1988, 29, 5739.
35. (h) Farina, V.; Baker, S.R.; Sapino, C. Tetrahedron Lett. 1988, 29, 6043.
36. (i) Kant, J.; Walker, D.G. In "The Organic Chemistry of β-Lactams," Georg, G.I., Ed.; VCH Publishers: New York, 1993; pp. 121-196.
37. 13C NMR spectroscopy, infrared spectroscopy, as well as high-resolution mass spectrometry and/or combustion analysis.
38. For a related example of a Stille reaction involving an indole nucleus, see Ciattini, P.G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1994, 35, 2405.
39. (a) Tsuji, J.; Takahashi, M.; Takahashi, T. Tetrahedron Lett. 1980, 21, 849.
40. (b) Fenton, D.M. J. Org. Chem. 1973, 38, 3192.
41. (c) Larock, R.C. J. Org. Chem. 1975, 40, 3237.
42. (d) Cassar, L.; Foa, M.; Gardano, A. J. Organometallic Chem. 1976, 121, C55.
43. (e) Fujiwara, Y.; Kawauchi, T.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1980, 220.
44. (f) Alper, H.; Hashem, K.; Heveling, J. Organometallics 1982, 1, 775.
45. In the carboxylation of beta-lactam 3, a small amount (5-10%) of thioester 12 is also obtained through a yet unidentified pathway. (equation presented)