Parallel solid-phase synthesis and structural characterization of a library of highly substituted chiral 1,3-oxazolidines

Journal of Combinatorial Chemistry

Volumn 2, Issue 6, 2000, Pages 698-709

  Tremblay, Martin R ^a   Wentworth Jr , Paul ^a   Lee Jr , George E ^a,b   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

CHROMATOGRAPHY, LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; OXAZOLES; STEREOISOMERISM;

EID: 0034320404     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0000500     Document Type: Article

References (47)

1. Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Nature 1991, 354, 84-86.
2. Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367-383.
3. Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419-6423.
4. Ecker, D. J.; Vickers, T. A.; Hanecak, R.; Driver, V.; Anderson, K. Nucleic Acids Res. 1993, 21, 1853-1856.
5. Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. J. Org. Chem. 1998, 63, 1126-1130.
6. Wentworth, P., Jr.; Janda, K. D. Curr. Opin. Biotech. 1998, 9, 109-115.
7. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
8. Norman, T. C.; Gray, N. S.; Koh, J. T.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 7430-7431.
9. Stankova, M.; Lebt, M. Mol. Diversity 1996, 2, 75-80.
10. Nugiel, D. A.; Cornelius, L. A. M.; Corbett, J. W. J. Org. Chem. 1997, 62, 201-203.
11. Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137-7138.
12. Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Salvino, J.; Leahy, E. M.; Sprengeler, P. A.; Furst, G.; Smith, A. B., III. J. Am. Chem. Soc. 1992, 114, 9217-9218.
13. Hirschmann, R.; Sprengeler, R. A.; Kawasaki, T.; Leahy, J. W.; Shakespeare, W. C.; Smith, A. B., III. J. Am. Chem. Soc. 1992, 114, 9699-9701.
14. Kocis, P.; Issakova, O.; Sepetove, N.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623-6626.
15. Carell, T.; Wintner, E. A.; Bahir-Hashemi, A.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1994, 33, 2059-2061.
16. Scolastico, C. Pure Appl. Chem. 1988, 60, 1689-1698.
17. Hoppe, I.; Hoffmann, H.; Gärtner, I.; Krettek, T.; Hoppe, D. Synthesis 1991, 1157-1162.
18. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8786.
19. Agami, C.; Couty, F.; Venier, O. Synlett 1995, 1027-1028.
20. Agami, C.; Comesse, S.; Kadouri-Puchot, C.; Lusinchi, M. Synlett 1999, 1094-1096.
21. Agami, C.; Couty, F.; Evano, G.; Mathieu, H. Tetrahedron 2000, 56, 367-376.
22. Agami, C.; Dechoux, L.; Melaimi, M. Org. Lett. 2000, 2, 633-634.
23. Moloney, G. P.; Craik, D. J.; Iskander, M. N.; Nero, T. L. J. Chem. Soc., Perkin Trans. 2 1998, 199-206.
24. Hoppe, I.; Hoppe, D.; Wolff, C.; Egert, E.; Herbst, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 67-69.
25. Neelakantan, L. J. Org. Chem. 1971, 36, 2256-2260.
26. Arséniyadis, S.; Huang, P. Q.; Morellet, N.; Beloeil, J.-C.; Husson, H.-P. Heterocycles 1990, 31, 1789-1799.
27. Takahashi, H.; Hsieh, B. C.; Higashiyama, K. Chem. Pharm. Bull. 1990, 38, 2429-2434.
28. Beckett, A. H.; Jones, G. R. Tetrahedron 1977, 33, 3313-3316.
29. Just, G.; Potvin, P.; Uggowitzer, P.; Bird, P. J. Org. Chem. 1983, 48, 2923-2924.
30. Agami, C.; Rizk, T. Tetrahedron 1985, 41, 537-540.
31. Hanson, R. M. Chem. Rev. 1991, 91. 437-474.
32. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
33. Cernerud, M.; Reina, J. A.; Tegenfeld, J.; Moberg, C. Tetrahedron: Asymmetry 1996, 7, 2863-2870.
34. Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem. 1991, 56, 5939-5942.
35. Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M. A.; Riera, A.; Sanders, J. K. M. J. Org. Chem. 1998, 63, 6309-6318.
36. Payne, G. B. J. Org. Chem. 1962, 27, 3819-3822.
37. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Wenging, Y.; Shäfer, W. Tetrahedron Lett. 1989, 30, 3943-3946.
38. Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333-93336.
39. Hu, Y.; Porco, J. A., Jr.; Labadie, J. W.; Gooding, O. W.; Trost, B. M. J. Org. Chem. 1998, 63, 4518-4521.
40. Hu, Y.; Porco, J. A., Jr. Tetrahedron Lett. 1998, 39, 2711-2714.
41. Lorgé, F.; Wagner, A.; Mioskowski, C. J. Comb. Chem. 1999, 1, 25-27.
42. Merino, P.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 1725-1729.
43. Andres, J. M.; Barrio, R.; Martinez, M. A.; Pedrosa, R.; Pérez-Encabo, A. J. Org. Chem. 1996, 61, 4210-4213.
44. Just, G.; Luthe, C.; Potvin, P. Tetrahedron Lett. 1982, 23, 2285-2290.
45. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
46. Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970-4982.
47. Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709-1713.