Stereoselective synthesis of constrained oxacyclic hydroxyethylene isosteres of aspartyl protease inhibitors. Nitroaldol methodology toward 2,3-substituted tetrahydrofurans

Tetrahedron

Volumn 60, Issue 35, 2004, Pages 7621-7628

  Hanessian, Stephen ^a   Brassard, Martin ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Amino acid; Amino alcohol; Catalysis; Enzyme inhibitor

Indexed keywords

ALDEHYDE DERIVATIVE; AMINOALCOHOL; ASPARTIC PROTEINASE INHIBITOR; BUTANE; ETHYLENE DERIVATIVE; LANTHANIDE; TETRAHYDROFURAN DERIVATIVE; ZINC;

ARTICLE; CATALYST; ISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 3843138591     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.060     Document Type: Article

References (58)

1. See for example, (a) Zeng L., Ye Q., Oberlies N.H., Shi G., Gu Z.-M., He K., McLaughlin J.L. Nat. Prod. Rep. 1996;275
2. McLaughlin J.L., Chang C., Smith D.L. Kinghorn A.D., Baladrin M.F. Human Medicinal Agents form Plants. 1993;117 American Chemical Society, Washington, DC. Chapter 9
3. Johnson H.A., Oberlies N.H., Alali F.Q., McLaughlin J.L. Bio. Act. Nat. Prod. 2000;173
4. See for example, (a) Ireland R.E., Vevert J.-P. J. Org. Chem. 45:1980;4259
5. For selected reviews on C-Glycosides, see (b) Postema M.H.D. Tetrahedron. 48:1992;8545
6. Levy D.E., Tang P.C. The Chemistry of C-glycosides. 1995;Pergamon, Oxford
7. For selected reviews, see Canan Kosh S.S., Chamberlin A.R. Atta-ur-Rahman. Studies in Natural Product Chemistry. Vol. 16:1995;687
8. See for example, (a) Negishi E., Kotora M. Tetrahedron. 53:1997;6707
9. Trost B.M., Tenaglia A. Tetrahedron Lett. 29:1988;2927
10. Evans D.A., Kozlowski M.C., Murry J.A., Burgey C.S., Campos K.R., Connell B.T., Staples R.J. J. Am. Chem. Soc. 121:1999;669
11. Burke S.D., Jiang L. Org. Lett. 3:2001;1953
12. For excellent reviews, see (a) Cooper J.B. Curr. Drug Targets. 3:2002;155
13. Fairlie D.P. J. Med. Chem. 43:2000;305
14. Bender S.L., Babine R.E. Chem. Rev. 97:1997;1359
15. Henry L. Bull. Soc. Chim. Fr. 13:1895;999
16. For recent reviews, see (a) Luzzio F.A. Tetrahedron. 57:2001;915
17. Ono N. The Nitro Group in Organic Synthesis. 2001;Wiley-VCH, New York. Chapter 3, p 30
18. Rosini G. Trost B.M., Heathcock C.H. Comprehensive Organic Synthesis. Vol. 2:1996;321 Pergamon, Oxford
19. Ballini R., Petrini M. Tetrahedron. 60:2004;1017
20. Seebach D., Beck B.K., Mukhopadhyay T., Thomas E. Helv. Chim. Acta. 65:1982;1101
21. Seebach D., Colvin E.W., Lehr F., Weller T. Chimia. 33:1979;1
22. Rosini G., Ballini R., Sorrenti P. Synthesis. 1983;1014
23. Hanessian S., Kloss J. Tetrahedron Lett. 26:1985;1261
24. Ballini R., Bosica G., Forconi P. Tetrahedron. 52:1996;1677
25. Ballini R., Bosica G. J. Org. Chem. 62:1997;425
26. Solladié-Cavallo A., Khiar N. J. Org. Chem. 55:1990;4750
27. See also Wollenberg R.H., Miller S.J. Tetrahedron Lett. 1978;3219
28. Hanessian S., Devasthale P.V. Tetrahedron Lett. 37:1996;987
29. See also Öhrlein R., Jäger V. Tetrahedron Lett. 29:1988;6083
30. Simoni D., Invidata F.P., Manfredini S., Ferroni R., Lampronti I., Roberti M., Pollini G.-P. Tetrahedron Lett. 38:1997;2749
31. Ma D., Pan Q., Han F. Tetrahedron Lett. 43:2002;9401
32. Davis A.P., Dempsey K.J. Tetrahedron: Asymmetry. 6:1995;2829
33. Chinchilla R., Nájera C., Sánchez-Agulló P. Tetrahedron: Asymmetry. 5:1994;1393
34. van Aken E., Wynberg H., van Bolhuis F. Chem. Commun. 1992;629
35. Kisanga P.B., Verkade J.G. J. Org. Chem. 64:1999;4298
36. Verkade J.G., Kisanga P.B. Aldrichimica Acta. 37:2004;3
37. Sasai H., Suzuki T., Arai S., Shibasaki M. J. Am. Chem. Soc. 111:1992;4418
38. Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187
39. Arai T., Yamada Y.M.A., Yamamoto N., Sasai H., Shibasaki M. Chem. Eur. J. 2:1996;1368
40. Sasai H., Tokunaga T., Watanabe S., Suzuki T., Itoh N., Shibasaki M. J. Org. Chem. 60:1995;7388
41. Trost B.M., Yeh V.S.C., Ito H., Bremeyer N. Org. Lett. 4:2002;2621
42. Trost B.M., Yeh V.S.C. Angew. Chem., Int. Ed. 41:2002;861
43. Christensen C., Juhl C., Jørgensen K.A. Chem. Commun. 2001;2222
44. Risgaard T., Gothelf K.V., Jørgensen K.A. Org. Biomol. Chem. 1:2003;153
45. Evans D.A., Seidel D., Rueping M., Lam H.W., Shaw J.T., Downey C.W. J. Am. Chem. Soc. 125:2003;12692
46. Corey E.J., Zhang F.-Y. Angew. Chem., Int. Ed. 38:1999;1931
47. Ooi T., Doda K., Maruoka K. J. Am. Chem. Soc. 125:2003;2054
48. Hanessian S., Murray P.J., Sahoo S.P. Tetrahedron Lett. 26:1985;5627
49. Hanessian S., Murray P.J. Tetrahedron. 43:1987;5055
50. Lieber E., Smith G.B.L. J. Am. Chem. Soc. 58:1936;1417
51. Levering D.R., Morritz F.L., Lieber E. J. Am. Chem. Soc. 72:1950;1190
52. Kende A.S., Mendoza J.S. Tetrahedron Lett. 32:1991;1699
53. Fitch R.W., Luzzio F.A. Tetrahedron Lett. 35:1994;6013
54. Osby J.O., Ganem B. Tetrahedron Lett. 26:1985;6413
55. Hanessian S., Gai Y., Wang W. Tetrahedron Lett. 37:1996;7473
56. (b) Wang, W. Ph.D. Dissertation, Université de Montréal, 1998.
57. Tarnus C., Rémy J.-M., d'Orchymont H. Bio. Med. Chem. 4:1996;1287
58. Kornblum N., Larson H.L., Blackwood R.K., Mooberry D.D., Graham O., Graham G.E. J. Am. Chem. Soc. 78:1956;1497