A new constrained proline analogue with an 8-azabicyclo[3.2.1]octane skeleton

Tetrahedron

Volumn 63, Issue 23, 2007, Pages 5056-5061

  Casabona, Diego ^a   Jiménez, Ana I ^a   Cativiela, Carlos ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Bicyclic proline; Constrained amino acid; Proline analogue; Quaternary amino acid; Ring closing metathesis

Indexed keywords

8 AZABICYCLO[3.2.1]OCTANE 1 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; PRIORITY JOURNAL; SKELETON; SYNTHESIS;

EID: 34247637200     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.115     Document Type: Article

References (60)

1. Cowell S.M., Lee Y.S., Cain J.P., and Hruby V.J. Curr. Med. Chem. 11 (2004) 2785-2798
2. Sagan S., Karoyan P., Lequin O., Chassaing G., and Lavielle S. Curr. Med. Chem. 11 (2004) 2799-2822
3. Venkatraman J., Shankaramma S.C., and Balaram P. Chem. Rev. 101 (2001) 3131-3152
4. Gibson S.E., Guillo N., and Tozer M.J. Tetrahedron 55 (1999) 585-615
5. Hruby V.J., Li G., Haskell-Luevano C., and Shenderovich M. Biopolymers (Pept. Sci.) 43 (1997) 219-266
6. Hanessian S., McNaughton-Smith G., Lombart H.-G., and Lubell W.D. Tetrahedron 53 (1997) 12789-12854
7. Rizo J., and Gierasch L.M. Annu. Rev. Biochem. 61 (1992) 387-418
8. Toniolo C., Crisma M., Formaggio F., and Peggion C. Biopolymers (Pept. Sci.) 60 (2001) 396-419
9. Kaul R., and Balaram P. Bioorg. Med. Chem. 7 (1999) 105-117
10. Benedetti E. Biopolymers (Pept. Sci.) 40 (1996) 3-44
11. For recent reviews on the synthesis of constrained α-amino acids see:
12. Lasa M., and Cativiela C. Synlett (2006) 2517-2533
13. Park K.-H., and Kurth M.J. Tetrahedron 58 (2002) 8629-8659
14. Cativiela C., and Díaz-de-Villegas M.D. Tetrahedron: Asymmetry 11 (2000) 645-732
15. Cativiela C., and Díaz-de-Villegas M.D. Tetrahedron: Asymmetry 9 (1998) 3517-3599
16. Reiersen H., and Rees A.R. Trends Biochem. Sci. 26 (2001) 679-684
17. Vanhoof G., Goossens F., De Meester I., Hendriks D., and Scharpé S. FASEB J. 9 (1995) 736-744
18. MacArthur M.W., and Thornton J.M. J. Mol. Biol. 218 (1991) 397-412
19. Berkessel A., and Gröger H. Asymmetric Organocatalysis (2005), Wiley-VCH, Weinheim
20. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
21. For some recent examples see:
22. Kawabata T., Matsuda S., Kawakami S., Monguchi D., and Moriyama K. J. Am. Chem. Soc. 128 (2006) 15394-15395
23. Chaume G., Van Severen M.-C., Marinkovic S., and Brigaud T. Org. Lett. 8 (2006) 6123-6126
24. Bitterman H., and Gmeiner P. J. Org. Chem. 71 (2006) 97-102
25. Amjad M., and Knight D.W. Tetrahedron Lett. 47 (2006) 2825-2828
26. Filosa R., Holder C., and Auberson Y.P. Tetrahedron Lett. 47 (2006) 8929-8932
27. Tayama E., Nanbara S., and Nakai T. Chem. Lett. 35 (2006) 478-479
28. Nájera C., and Sansano J.M. Angew. Chem., Int. Ed. 44 (2005) 6272-6276
29. Ooi T., Miki T., and Maruoka K. Org. Lett. 7 (2005) 191-193
30. Maeda K., Miller R.A., Szumigala Jr. R.H., Shafiee A., Karady S., and Armstrong III J.D. Tetrahedron Lett. 46 (2005) 1545-1549
31. Karoyan P., Sagan S., Lequin O., Quancard J., Lavielle S., and Chassaing G. In: Attanasi O.A., and Spinelli D. (Eds). Substituted Prolines: Syntheses and Applications in Structure-Activity Relationship Studies of Biologically Active Peptides. Targets in Heterocyclic Systems. Chemistry and Properties Vol. 8 (2005), Royal Society of Chemistry, Cambridge 216-273
32. Chen C., Li X., and Schreiber S.L. J. Am. Chem. Soc. 125 (2003) 10174-10175
33. Avenoza A., Cativiela C., Busto J.H., Fernández-Recio M.A., Peregrina J.M., and Rodríguez F. Tetrahedron 57 (2001) 545-548
34. For the synthesis of 2,5-ethanoproline bearing additional substituents see:
35. Gil A.M., Orús E., López-Carrillo V., Buñuel E., and Cativiela C. Tetrahedron: Asymmetry 16 (2005) 3115-3123
36. Gil A.M., Buñuel E., López P., and Cativiela C. Tetrahedron: Asymmetry 15 (2004) 811-819
37. Gil A.M., Buñuel E., Díaz-de-Villegas M.D., and Cativiela C. Tetrahedron: Asymmetry 14 (2003) 1479-1488
38. Buñuel E., Gil A.M., Díaz-de-Villegas M.D., and Cativiela C. Tetrahedron 57 (2001) 6417-6427
39. Campbell J.A., and Rapoport H. J. Org. Chem. 61 (1996) 6313-6325
40. Alonso de Diego S.A., Gutierrez-Rodríguez M., Pérez de Vega M.J., Casabona D., Cativiela C., González-Muñiz R., Herranz R., Cenarruzabeitia E., Frechilla D., Del Río J., Jimeno M.L., and García-López M.T. Bioorg. Med. Chem. Lett. 16 (2006) 1392-1396
41. Han W., Pelletier J.C., Mersinger L.J., Kettner C.A., and Hodge C.N. Org. Lett. 1 (1999) 1875-1877
42. Alemán C., Jiménez A.I., Cativiela C., Pérez J.J., and Casanovas J. J. Phys. Chem. B 109 (2005) 11836-11841
43. Gil A.M., Buñuel E., Jiménez A.I., and Cativiela C. Tetrahedron Lett. 44 (2003) 5999-6002
44. Avenoza A., Busto J.H., Peregrina J.M., and Rodríguez F. J. Org. Chem. 67 (2002) 4241-4249
45. Spande T.F., Garraffo H.M., Edwards M.W., Yeh H.J.C., Pannell L., and Daly J.W. J. Am. Chem. Soc. 114 (1992) 3475-3478
46. Sato T., Kugo Y., Nakaumi E., Ishibashi H., and Ikeda M. J. Chem. Soc., Perkin Trans. 1 (1995) 1801-1809
47. Zhang W., and Pugh G. Tetrahedron 59 (2003) 3009-3018
48. Kotha S., and Sreenivasachary N. Bioorg. Med. Chem. Lett. 8 (1998) 257-260
49. In: Grubbs R.H. (Ed). Handbook of Metathesis (2003), Wiley-VCH, Weinheim
50. Kapferer P., and Vasella A. Helv. Chim. Acta 87 (2004) 2764-2789
51. See, for example:
52. Cheng J., and Trudell M.L. Org. Lett. 3 (2001) 1371-1374
53. Olivo H.F., Hemenway M.S., and Gezginci M.H. Tetrahedron Lett. 39 (1998) 1309-1312
54. Hassner A., and Belostotskii A.M. Tetrahedron Lett. 36 (1995) 1709-1712
55. Fletcher S.R., Baker R., Chambers M.S., Herbert R.H., Hobbs S.C., Thomas S.R., Verrier H.M., Watt A.P., and Ball R.G. J. Org. Chem. 59 (1994) 1771-1778
56. Broka C.A. Tetrahedron Lett. 34 (1993) 3251-3254
57. Nelsen S.F., Ippoliti J.T., Frigo T.B., and Petillo P.A. J. Am. Chem. Soc. 111 (1989) 1776-1781
58. Pinder A.R. Synthesis (1980) 425-452
59. Sheldrick G.M. SHELXS-97, Program for the Solution of Crystal Structures (1997), University of Göttingen, Göttingen
60. Sheldrick G.M. SHELXL-97. Program for the Refinement of Crystal Structures (1997), University of Göttingen, Göttingen