Total asymmetric synthesis of highly constrained amino acids β-isopropyl-2',6'-dimethyl-tyrosines

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5135-5138

  Han, Yinglin ^a   Liao, Subo ^a   Qiu, Wei ^a   Cai, Chaozhong ^a   Hruby, Victor J ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; TYROSINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0030745855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01094-0     Document Type: Article

References (36)

1. (a) Hruby, V.J. Life Sciences, 1982, 31, 189-199.
2. (b) Veber, D.F.; Freidinger, R.M. Trends Neurosci. 1985, 8, 392-396.
3. (c) Kessler, H. Angew. Chem. Int. Ed. Engl. 1982, 21, 512-513.
4. (d) Mosberg, H.I.; Hurst, R.; Hruby, V.J.; Gee, K.; Yamamura, H.I.; Galligan, J.J.; Burks, T.F. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 5871-5874.
5. (e) Milner-White, E.J. Trends Pharm. Sci. 1989, 10, 70-74.
6. (f) Kazmierski, W.; Wire, S.W.; Liu, G.K.; Knapp, R.J.; Shook, J.E.; Burks, T.F.; Yamamura, H.I.; Hruby, V.J. J. Med. Chem. 1988, 31, 2170-2177.
7. (g) Hruby, V.J.; Tóth, G.; Gehrig, C.A.; Kao, L.-F.; Knapp, R.; Liu, G.K.; Yamamura, H.K.; Kramer, T.H.; Davis, P.; Burks, T.F. J. Med. Chem. 1991, 34, 1823-1830.
8. (a) Dharanipragada, R.; VanHulle, K.; Bannister, A.; Bear, S.; Kennedy, L.; Hruby, V. J. Tetrahedron 1992, 48, 4733-4748;
9. (b) Nicolas, E.; Russell, K.C.; Hruby, V.J. J. Org. Chem. 1993, 58, 766-770;
10. (c) Nicolas, E.; Russell, K.C.; Knollenberg, J.; Hruby, V.J. J. Org. Chem. 1993, 58, 7565 -7571;
11. (d) Jiao, D.; Russell, K.C.; Hruby, V.J. Tetrahedron 1993, 49, 3511-3520;
12. (e) Li, G.; Patel, D.; Hruby, V.J. J. Chem. Soc. Perkin Trans. 1 1994, 3057-3059;
13. (f) Qian, X.; Russell, K. C.; Boteju, L.W.; Hruby, V. J. Tetrahedron 1995, 57, 1033-1054.
14. (g) Liao, S.; Hruby, V.J. Tetrahedron. Lett. 1996, 37, 1563-1566;
15. (h) Li, G.; Jarosinski, M.A.; Hruby, V.J. Tetrahedron Lett, 1993, 34, 2561-2564;
16. (i) Li, G.; Patel D.; Hruby, V.J. Tetrahedron Lett. 1994, 35, 2301-2304;
17. (j) Kazmierski, W.M.; Hruby, V.J. Tetrahedron Lett. 1991, 32, 5769-5772;
18. (k) Boteju, L.W.; Wegner, K.; Hruby, V.J. Tetrahedron Lett. 1992, 33, 7491-7494.
19. (a) Hruby, V.J.; Fang, S.N.; Tóth, G.; Jiao, D.; Matsunaga T.O.; Collins, N.; Knapp, R.; Yamamura, H.I. Peptide 1990, Proceedings of the 21st European Peptide Symposium, E. Giralt and D. Andreu, eds., ESCOM Publishers, Leiden, The Netherlands;
20. (b) Lebl, M.; Tóth, G.; Slaninová, J.; Hruby, V.J. Int. J. Peptide Protein Res. 1992, 39, 401-414;
21. (c) Töth, G.; Russell, K.C.; Landis, G.; Kramer, T.H.; Fang, L.; Knapp, R.; Davis, P.; Burks, T.F.; Yamamura, H.I.; Hruby, V.J. J. Med. Chem. 1992, 35, 2384-2391;
22. (d) Nikiforovich, G.V.; Prakash, O.; Gehrig, C.A.; Hruby, V.J. Int. J. Peptide Res. 1993, 41, 347-361;
23. (e) Qian, X.; Kövér, K.E.; Shenderovich, M.D.; Misicka, A.; Zalewska, T.; Horvath, R.; Davis, P.; Porreca, F.; Yamamura, H.I.; Hruby, V.J. J. Med. Chem.. 1994, 37, 1746-1757;
24. (f) Shenderovich, M.D.; Kövér, K.E.; Nikiforovich, G.V., Jiao, D.; Hruby, V.J. Biopolymers 1996, 38, 141-156;
25. (g) Haskell-Luevano, C.; Boteju, L.W.; Miwa, H.; Dickinson, C.; Gantz, I.; Yamada, T.; Hadley, M.E.; Hruby, V.J. J. Med. Chem. 1995, 38, 4720-4729;
26. (h) Azizeh, B.Y.; Shenderovich, M.D.; Trivedi, D.; Li, G.; Sturm, N.S.; Hruby, V.J. J. Med. Chem.. 1996, 39, 2449-2455.
27. (a) Hruby, V. J. Biopolymers 1993, 33, 1073-1082
28. (b) Toniolo, C. Int. J. Pep.Protein Res. 1990, 35, 287-300.
29. (c) Hruby, V.J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249-262.
30. Pirrung, M.C.; Han, H.; Ludwig, R.T. J. Org. Chem. 1994, 59, 2430-2436.
31. Evans, D.A.; Weber, A.E. J. Am. Chem. Soc. 1986, 108, 6757-6761.
32. Liao, S.; Han, Y.; Qiu, W.; Bruck, M.; Hruby, V.J. Tetrahedron Lett. 1996, 37, 7917-7920.
33. Evans, D.A.; Britton, T.C.; Ellman, J.A.; Dorow, R.L. J. Am. Chem. Soc. 1990, 112, 4011-4030.
34. Papa, A. J. J. Org. Chem. 1966, 31, 1426-1430.
35. Will be deposited with the Cambridge Crystallographic Data Centre.
36. 22D=-38.77 (c 0.127, MeOH).