Glycomimetics: A Versatile de Novo Synthesis of β-1-C-Aryl-deoxymannojirimycin Analogues

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 6046-6050

  Johnson, Carl R ^a   Johns, Brian A ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYMANNONOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN DERIVATIVE; GLYCOSIDASE INHIBITOR;

ARTICLE; DIABETES MELLITUS; DIGESTION; DRUG STABILITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; VIRUS INFECTION;

EID: 0030858181     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970585o     Document Type: Article

References (53)

1. (a) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
2. (b) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
3. (c) Fleet, G. W. J.; Karpas, A.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P. W.; Son, J. C.; Wilson, F. X.; Witty, D. R.; Jacob, G. S.; Rademacher, T. W. FEBS Lett. 1988, 237, 128.
4. (d) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182.
5. (e) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 135
6. (a) Sunkara, P. S.; Bowlin, T. L.; Liu, P. S.; Sjoerdsma, A. Biochem. Biophys. Res. Commun. 1987, 148, 206.
7. (b) Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74.
8. (c) Walker, B. D.; Kowalski, M.; Goh, W. C.; Kozarsky, K.; Krieger, M.; Rosen, C.; Rohrschneider, L.; Haseltine, W. A.; Sodroski, J. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8120.
9. (d) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9229.
10. (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215.
11. (b) Spearman, M. A.; Jamieson, J. C.; Wright, J. A. Exp. Cell Res. 1987, 168, 116.
12. (a) Truscheit, E.; Frommer, W.; Junge, B.; Müller, L; Schmidt, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744.
13. (b) Horii, S.; Fukase, H.; Matsuo, T.; Kameda, Y.; Asano, N.; Matsui, K. J. Med. Chem. 1986, 29, 1038.
14. (c) Anzeveno, P. B.; Creemer, L. J.; Daniel, J. K.; King, C.-H. R.; Liu, P. S. J. Org. Chem. 1989, 54, 2539.
15. (a) Jensen, J. L.; Tsuang, S. C.; Uslan, A. H. J. Org. Chem. 1986, 57, 816.
16. (b) Liu, P. S. J. Org. Chem. 1987, 52, 4717.
17. (c) Cogoli, A.; Semenza, G. J. Biol. Chem. 1975, 250, 7802.
18. (d) Sinnot, M. L. Chem. Rev. 1990, 90, 1171.
19. Winchester, B.; Barker, C.; Baines, S.; Jacob, G. S.; Namgoong, S. K.; Fleet, G. W. J. Biochem. J. 1990, 265, 277.
20. For a recent example of an azasugar thioglycoside see Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 35, 4119.
21. (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton. FL, 1995.
22. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Elsevier Science: Oxford, 1995.
23. (c) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
24. (a) Kite, G. C.; Fellows, L. E.; Fleet, G. W. J.; Liu, P. S.; Scofield, A. M.; Smith, N. G. Tetrahedron Lett. 1988, 29, 6483.
25. (b) Fleet, G. W. J.; Namgoong, S. K.; Barker, C.; Baines, S.; Jacob, G. S.; Winchester, B. Tetrahedron Lett. 1989, 30, 4439.
26. (c) Liotta, L. J.; Lee, J.; Ganem, B. Tetrahedron 1991, 47, 2433.
27. (d) Bruce, I.; Fleet, G. W. J.; di Bello, C.; Wincheser, B. Tetrahedron 1992, 48, 10191.
28. (e) Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359.
29. (f) Holt, K. E.; Leeper, F. J.; Handa, S. J. Chem. Soc., Perkin Trans. 1 1994, 231.
30. (g) Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799.
31. (h) Martin, O. R.; Xie, F.; Liu, L. Tetrahedron Lett. 1995, 36, 4027.
32. (i) Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
33. (a) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991.
34. (b) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483.
35. (c) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991.
36. (d) Frérot, E.; Marquis, C.; Vogel, P. Tetrahedron Lett. 1996, 37, 2023.
37. (e) Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987.
38. (f) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R. J. Am. Chem. Soc. 1997, 119, 4856.
39. Böshagen, H.; Geiger, W.; Junge, B. Angew. Chem., Int. Ed. Engl. 1981, 20, 806.
40. The diol derived from bromobenzene is now prepared in crystalline form on a multikilogram scale by Genecor International, Inc., Rochester, NY. For a nice overview of applications of such cis-cyclohexadienediols see Hudlickly, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993.
41. (a) Miyaura, N.; Yanagi, T.; Susuki, A. Synth. Commun. 1981, 11, 513.
42. (b) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749.
43. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
44. (a) Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014.
45. (b) Braun, M. P. Ph.D. Dissertation, Wayne State University, 1995.
46. (2-Nitrophenyl)boronic acid has been cited as a sluggish coupling partner under similar conditions see Thompson, W. J; Gaudino, J. J. Org. Chem. 1984, 49, 5237.
47. Complex mixtures of several boronic acid/anhydride species have also been noted by Hoye; see Hoye, T. R; Chen, M. J. Org. Chem. 1996, 61, 7940. These mixtures are difficult to characterize but fortunately present no problems when subjected in crude form to the Suzuki cross-coupling conditions resulting in only the desired coupled products.
48. Johnson, C. R.; Johns, B. A. Manuscript in preparation.
49. Eggers, C. A.; Kettle, S. F. A. Inorg. Chem. 1967, 6, 160.
50. Diorazio, L. J.; Widdowson, D. A.; Clough, J. M. Tetrahedron 1992, 48, 8073.
51. Gleave, C. A.; Sutherland, I. O.; J. Chem. Soc., Chem. Commun. 1994, 1873.
52. Müller, W.; Kipfer, P.; Lowe, D. A.; Urwyler, S. Helv. Chim. Acta 1995, 78, 2026.
53. Sharp, M. J.; Cheng, W.; Snieckus, V. Tetrahedron Lett. 1987, 28, 5093.