A stereocontrolled, convergent synthesis of hydroxyethylene dipeptide isosteres

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6240-6244

  Tao, Junhua ^a   Hoffman, Robert V ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE DERIVATIVE; HYDROXYETHYLENE DIPEPTIDE ISOSTERE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BLOOD PRESSURE REGULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; NONHUMAN; PROTEINASE INHIBITION; STEREOCHEMISTRY;

EID: 0030772545     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970579s     Document Type: Article

References (46)

1. Sandler, M.; Smith, H. J. Design of Enzyme Inhibitors as Drugs; Oxford Press; Oxford, U.K., 1989.
2. (a) Rich, D. H. Peptidase Inhibitors. In Comprehensive Medicinal Chemistry; Sammes, P. G., Ed.; Pergamon Press: Oxford, U.K., 1990; pp 391-441.
3. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
4. Peach, M. J. Physiol. Rev. 1977, 57, 313.
5. (a) Kramer, R. A.; Schaber, M. D.; Skalka, A. M.; Ganguly, K.; Wong-Staal, F.; Reddy, E. P. Science 1986, 231, 1580.
6. (b) Kohl, N. E.; Emini, E. A.; Schleis, W. A.; Davis, L. J.; Heimbach, J. C.; Dixon, R. A.; Scolnik, E. M.; Sigal, I. S. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4686.
7. The S stereochemical designation may change to R for certain side chains because of Cahn-Ingold-Prelog priority rules, but the stereochemical orientation of the side chain would be the same.
8. It has been found that extended binding regions can alter the S preference in HIV-1 protease and potentially other proteases as well. Rich, D. H.; Sun, C.-Q.; Vara Prasad, J. V. N.; Pathiasseril, A.; Toth, M. V.; Marshall, G. R.; Clare, M.; Mueller, R. A.; Houseman, K. J. Med. Chem. 1991, 34, 1222.
9. Dreyer, G. B.; Metcalf, B. W.; Tomaszek, T. A., Jr.; Carr, T. J.; Chandler, A. C., III; Hyland, L.; Farkhoury, S. A.; Magaad, V. W.; Moore, M. L.; Strickler, J. E.; Debouk, C.; Meek, T. D. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9752.
10. Kempf, D. J.; Norbeck, D. W.; Codacovi, L.; Wang, X. C.; Kohlbrenner, W. F.; Wideburg, N. E.; Saldivar, A.; Craig-Kennard, A.; Vasavanonda, S.; Clement, J. J.; Erickson J. in Recent Advances in the Chemistry of Anti-Infective Agents; Bentley, P. H., Ed.; Royal Society of Chemistry: Cambridge, 1993; pp 297-313.
11. Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 2247 and references therein.
12. Szelke, M.; Jones, M. D.; Atrash, B.; Hallet, A.; Leckie, B. J. Proc. Am. Pept. Symp. 8th 1983, 579
13. Rich, D. H.; Salituro, F. G.; Holliday, M. W. Proc. Am. Pept. Symp. 8th 1983, 511.
14. Representative examples; (a) Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183. (b) Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org. Chem. 1993, 58, 2286. (d) D'Aniello, F.; Gehanne, S.; Taddei, M. Tetrahedron Lett. 1992, 33, 5621. (e) Thompson, W. J.; Ball, R. G.; Darke, P. L.; Zugay, J. A.; Thies, J. E. Tetrahedron Lett. 1992, 33, 2957. (f) Kano, S.;Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233. (g) Fray, A. H.; Kaye, R. L.; Kleinman, E. F. J. Org. Chem. 1986, 51, 4828. (h) Kempf, D. J. J. Org. Chem. 1988, 51, 3921.
15. Representative examples; (a) Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183. (b) Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org. Chem. 1993, 58, 2286. (d) D'Aniello, F.; Gehanne, S.; Taddei, M. Tetrahedron Lett. 1992, 33, 5621. (e) Thompson, W. J.; Ball, R. G.; Darke, P. L.; Zugay, J. A.; Thies, J. E. Tetrahedron Lett. 1992, 33, 2957. (f) Kano, S.;Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233. (g) Fray, A. H.; Kaye, R. L.; Kleinman, E. F. J. Org. Chem. 1986, 51, 4828. (h) Kempf, D. J. J. Org. Chem. 1988, 51, 3921.
16. Representative examples; (a) Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183. (b) Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org. Chem. 1993, 58, 2286. (d) D'Aniello, F.; Gehanne, S.; Taddei, M. Tetrahedron Lett. 1992, 33, 5621. (e) Thompson, W. J.; Ball, R. G.; Darke, P. L.; Zugay, J. A.; Thies, J. E. Tetrahedron Lett. 1992, 33, 2957. (f) Kano, S.;Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233. (g) Fray, A. H.; Kaye, R. L.; Kleinman, E. F. J. Org. Chem. 1986, 51, 4828. (h) Kempf, D. J. J. Org. Chem. 1988, 51, 3921.
17. Representative examples; (a) Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183. (b) Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org. Chem. 1993, 58, 2286. (d) D'Aniello, F.; Gehanne, S.; Taddei, M. Tetrahedron Lett. 1992, 33, 5621. (e) Thompson, W. J.; Ball, R. G.; Darke, P. L.; Zugay, J. A.; Thies, J. E. Tetrahedron Lett. 1992, 33, 2957. (f) Kano, S.;Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233. (g) Fray, A. H.; Kaye, R. L.; Kleinman, E. F. J. Org. Chem. 1986, 51, 4828. (h) Kempf, D. J. J. Org. Chem. 1988, 51, 3921.
18. Representative examples; (a) Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183. (b) Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org. Chem. 1993, 58, 2286. (d) D'Aniello, F.; Gehanne, S.; Taddei, M. Tetrahedron Lett. 1992, 33, 5621. (e) Thompson, W. J.; Ball, R. G.; Darke, P. L.; Zugay, J. A.; Thies, J. E. Tetrahedron Lett. 1992, 33, 2957. (f) Kano, S.;Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233. (g) Fray, A. H.; Kaye, R. L.; Kleinman, E. F. J. Org. Chem. 1986, 51, 4828. (h) Kempf, D. J. J. Org. Chem. 1988, 51, 3921.
19. Representative examples; (a) Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183. (b) Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org. Chem. 1993, 58, 2286. (d) D'Aniello, F.; Gehanne, S.; Taddei, M. Tetrahedron Lett. 1992, 33, 5621. (e) Thompson, W. J.; Ball, R. G.; Darke, P. L.; Zugay, J. A.; Thies, J. E. Tetrahedron Lett. 1992, 33, 2957. (f) Kano, S.;Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233. (g) Fray, A. H.; Kaye, R. L.; Kleinman, E. F. J. Org. Chem. 1986, 51, 4828. (h) Kempf, D. J. J. Org. Chem. 1988, 51, 3921.
20. Representative examples; (a) Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183. (b) Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org. Chem. 1993, 58, 2286. (d) D'Aniello, F.; Gehanne, S.; Taddei, M. Tetrahedron Lett. 1992, 33, 5621. (e) Thompson, W. J.; Ball, R. G.; Darke, P. L.; Zugay, J. A.; Thies, J. E. Tetrahedron Lett. 1992, 33, 2957. (f) Kano, S.;Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233. (g) Fray, A. H.; Kaye, R. L.; Kleinman, E. F. J. Org. Chem. 1986, 51, 4828. (h) Kempf, D. J. J. Org. Chem. 1988, 51, 3921.
21. Representative examples; (a) Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183. (b) Konieczny, M. T.; Toma, P. H.; Cushman, M. J. Org. Chem. 1993, 58, 4619. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org. Chem. 1993, 58, 2286. (d) D'Aniello, F.; Gehanne, S.; Taddei, M. Tetrahedron Lett. 1992, 33, 5621. (e) Thompson, W. J.; Ball, R. G.; Darke, P. L.; Zugay, J. A.; Thies, J. E. Tetrahedron Lett. 1992, 33, 2957. (f) Kano, S.;Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233. (g) Fray, A. H.; Kaye, R. L.; Kleinman, E. F. J. Org. Chem. 1986, 51, 4828. (h) Kempf, D. J. J. Org. Chem. 1988, 51, 3921.
22. (a) Lagu, B. R.; Liotta, D. C. Tetrahedron Lett. 1994, 35, 547.
23. (b) Radunz, H.-E.; Eierman, V.; Schneider, G.; Riethmuner, A. Tetrahedron 1991, 47, 1887.
24. (a) Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771 and references therein.
25. (b) Evans, B. E.; Rittle, K. E.; Homnick, C. F.; Springer, J. P.; Hirshfield, J.; Veber, P. F. J. Org. Chem. 1985, 50, 4615.
26. (a) Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem. 1995, 60, 7927 and references therein.
27. (b) Poss, M. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411.
28. (c) Boyd, S. A.; Mantei, R. A.; Hsiao, C.-N.; Baker, W. R. J. Org. Chem. 1991, 56, 438.
29. Plata, D. J.; Leanna, M. R.; Morton, H. E. Tetrahedron Lett. 1991, 32, 3623.
30. (a) Chakraborty, T. K.; Gangakhedkar, K. K. Synth. Commun. 1996, 26, 2045 and references therein.
31. (b) Ghosh, A. K.; McKee, S. P.; Thompson, W. J. J. Org. Chem. 1991, 56, 6500.
32. (c) Shiozaki, M.; Kobayashi, Y. Tetrahedron 1991, 47, 2785.
33. Sakurai, M.; Hata, T.; Yabe, Y. Tetrahedron Lett. 1993, 34, 5939.
34. Peyrat, J.-F.; Chaboche, C.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1995, 36, 2757.
35. Wuts, P. G. M.; Ritter, A. R.; Pruitt, L. E. J. Org. Chem. 1992, 57, 6696.
36. Hoffman, R. V.; Kim, H.-O. Tetrahedron Lett. 1992, 33, 3579.
37. Hoffman, R. V.; Kim, H.-O. Tetrahedron Lett. 1993, 34, 2051.
38. Hoffman, R. V.; Kim, H.-O. J. Org. Chem. 1995, 60, 5107.
39. Hoffman, R. V.; Tao, J.-H. Tetrahedron, submitted.
40. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531 and references therein.
41. (a) Hoffman, R. V.; Kim, H.-O. Tetrahedron 1992, 48, 3007 and references therein.
42. (b) Xiang, Y. B.; Snow, K.; Belley, M. J. Org. Chem. 1993, 58, 993 and references therein.
43. Hoffman, R. V.; Tao, J.-H. J. Org. Chem. 1997, 62, 2292.
44. For calibrating the LIS method to determine enantioselectivity, racemic 4a was prepared and converted to racemic 3aa which was examined by the LIS reagent.
45. Bajwa, J. S. Tetrahedron Lett. 1992, 33, 2955.
46. Distilled from absolute methanol using Mg turnings and iodine. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: Oxford, U.K., 1988; p 217.