Stereoselective solid-phase synthesis of β-lactams - A novel cyclization/cleavage step towards 1-oxacephams

Angewandte Chemie - International Edition

Volumn 38, Issue 8, 1999, Pages 1121-1123

  Furman, Bartłomiej ^a   Thürmer, René ^b   Kałuza, Zbigniew ^a   Łysek, Robert ^a   Voelter, Wolfgang ^b   Chmielewski, Marek ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Antibiotics; Cyclizations; Lactams; Solid phase synthesis

Indexed keywords

1 OXACEPHEM DERIVATIVE; BETA LACTAM ANTIBIOTIC;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033583509     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990419)38:8<1121::AID-ANIE1121>3.0.CO;2-D     Document Type: Article

References (36)

1. Reviews: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zachel, Angew. Chem. 1996, 108, 2436-2487;
2. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337;
3. b) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600;
4. c) R. C. D. Brown, J. Chem. Soc. Perkin Trans. 1 1998, 3293-3320.
5. a) B. Ruhland, A. Bhandari, E. M. Gordon, M. A. Gallop, J. Am. Chem. Soc. 1996, 118, 253-254;
6. b) B. Ruhland, A. Bombrun, M. A. Gallop, J. Org. Chem. 1997, 62, 7820-7826;
7. c) Y. Pei, R. A. Houghten, J. S. Kiely, Tetrahedron Lett. 1997, 38, 3349-3352;
8. d) E. G. Matta, Tetrahedron Lett. 1997, 38, 6335-6338;
9. g) V. Molteni, R. Annunziata, H. Cinquini, F. Cozzi, M. Benaglia, Tetrahedron Lett. 1998, 39, 1257-1260.
10. a) W. Nagata, Pure Appl. Chem. 1989, 61, 325-336;
11. b) S. Shibahara, T. Okonogi, Y. Murai, T. Kudo, T. Yoshida, S. Kondo, B. G. Christensen, J. Antibiot. 1988, 41, 1154-1157;
12. c) H. C. Neu in The Chemistry of β-Lactams (Ed.: M. I. Page), Blackie, Glasgow, 1992, pp. 101-128.
13. a) Z. Kałuża, S. H. Park, Synlett 1996, 895-896;
14. b) Z. Kałuża, R. Łysek, Tetrahedron: Asymmetry 1997, 8, 2553-2560.
15. Z. Kałuża, Tetrahedron Lett. 1999, 40, 1025-1026
16. a) D. Hoppe, T. Hilpert, Tetrahedron 1987, 43, 2467-2474;
17. b) S. De Bernardo, J. P. Tengi, G. J. Sasso, M. Weigele, J. Org. Chem. 1985, 50, 3457-3462;
18. c) M. Murakami, M. Matsuura, T. Aoki, W. Nagata, Synlett 1990, 681-683;
19. d) M. Murakami, T. Aoki, W. Nagata, Synlett 1990, 684-686.
20. S. Hobbs DeWitt, J. S. Kiely, C. J. Stankovic, M. C. Schroeder, D. M. Reynolds Cody, M. R. Pavia, Proc. Natl. Acad. Sci. USA 1993, 90, 6909-6913.
21. a) B. A. Dressman, L. A. Spangle, S. W. Kaldor, Tetrahedron Lett. 1996, 37, 937-940;
22. b) S. A. Kolodziej, B. C. Hamper, Tetrahedron Lett. 1996, 37, 5277-5280;
23. c) L. F. Tietze, A. Steinmetz, Synlett 1996, 667-668;
24. d) L. F. Tietze, A. Steinmetz, F. Balkenhohl, Bioorg. Med. Chem. Lett. 1997, 7, 1303-1306;
25. e) J. Matthews, R. A. Rivero, J. Org. Chem. 1997, 62, 6090-6092;
26. f) S. W. Kim, S. Y. Ahn, J. S. Koh, J. H. Lee, S. Ro, H. Y. Cho, Tetrahedron Lett. 1997, 38, 4603-4606;
27. g) J. Stadlwieser, E. P. Ellmerer-Müller, A. Takó, N. Maslouh, W. Bannwarth, Angew. Chem. 1998, 110, 1487-1489;
28. Angew. Chem. Int. Ed. 1998, 37, 1402-1404;
29. h) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294;
30. i) K. H. Park, E. Abbate, S. Najdi, M. M. Olmstead, M. J. Kurth, Chem. Commun. 1998, 1679-1680.
31. J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser, C. G. Kruse, Tetrahedron Lett. 1996, 37, 8249-8252.
32. K. C. Nicolaou, J. Pastor, N. Winssinger, F. Murphy, J. Am. Chem. Soc. 1998, 120, 5132-5133.
33. a) S. Hanessian, F. Xie, Tetrahedron Lett. 1998, 39, 733-736;
34. b) S. Hanessian, F. Xie, Tetrahedron Lett. 1998, 39, 737-740.
35. a) Z. Kałuża, B. Furman, M. Patel, M. Chmielewski, Tetrahedron: Asymmetry 1994, 5, 2179-2186;
36. b) B. Furman, Z. Kałuża, M. Chmielewski, J. Org. Chem. 1997, 62, 3135-3139.