Stereoselective synthesis of new conduramines and aminocyclitol derivatives

Synlett

Volumn , Issue 11, 1998, Pages 1237-1239

  Jotterand, Nathalie ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001779302     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1909     Document Type: Article

References (53)

1. Rinehart, Jr., K. L.; Stroshane, R. M. J. Antibiotics 1976, 29, 319;
2. Rinehart, Jr., K. L.; Shield, L. S. "Aminocyclitol Antibiotics", ACS Symposium Series 125, Rinehart, Jr., K. L.; Suami, T. Eds., American Chemical Society: Washington, D. C. 1980, 1;
3. Aminoglycoside Antibiotics, Umezawa, H.; Hooper, I. R. Eds, Springer: New York, Heidelberg, 1982.
4. Moazed, D.; Noller, H. F. Nature 1987, 327, 389;
5. von Ahsen, U.; Davies, J.; Schroeder, R. Nature Ibid. 1991, 353, 368;
6. J. Mol. Biol. 1992, 226, 935;
7. Stage, T. K.; Hertel, K. J.; Uhlenbeck, O. C. RNA 1995, 1, 95;
8. Cloet-d'Orval, B.; Stage, T. K.; Uhlenbeck, O. C. Biochemistry 1995, 34, 11186.
9. Hendrix, M.; Alper, P. B.; Priestley, E. S.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1997, 36, 95.
10. Zapp, M. L.; Stern, S.; Green, M. R. Cell 1993, 74, 969;
11. Werstuck, G; Zapp, M. L.; Green, M. R. Chem. Biol. 1996, 3, 129.
12. Mei, H.-Y.; Galan, A. A.; Halim, N. S.; Mack, D. P.; Moreland, D. W.; Sanders, K. B.; Truong, H. N.; Czarnik, A. W. Bioorg. Med. Chem. Lett. 1995, 5, 2755.
13. Wang, H.; Tor, Y. J. Am. Chem. Soc. 1997, 119, 8734.
14. Wang, H.; Tor, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 109.
15. See e.g.: Legler, G; Bause, E. Carbohydr. Res. 1973, 28, 45;
16. Legler, G. Mol. Cell. Biochem. 1973, 2, 31;
17. Umezawa, W. Adv. Carbohydr. Chem. Biochem. 1974, 30, 111;
18. Horii, S.; Fukase, H.; Kameda, Y.; Asano, N.; Matsui, K. J. Med. Chem. 1986, 29, 1038;
19. Vertesy, L.; Fehlhaber, H.-W.; Schulz, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 1844;
20. Chandler, M.; Conroy, R.; Cooper, A. W. J.; Lamont, R. B.; Scicinski, J. J.; Smart, J. E.; Storer, R.; Weir, N. G.; Wilson, R. D. J.; Wyatt, P. G. J. Chem. Soc., Perkin Trans I 1995, 1189;
21. Ogawa, S.; Ashiura, M.; Uchida, C.; Watanabe, S.; Yamazaki, C.; Yamagishi, K.; Inokuchi, J.-i. Bioorg. Med. Chem. Lett. 1996, 6, 929;
22. Lew, W.; Williams, M. A.; Mendel, D. B.; Escarpe, P. A.; Kim, C. U. Bioorg. Med. Chem. Lett. 1997, 7, 1843;
23. Sears, P.; Wong, C.-H. J. Chem. Soc., Chem. Commun 1998, 1161 and ref. cited therein.
24. See e.g.: Kowarski, C. R.; Sarel, S. J. Org. Chem. 1973, 38, 117;
25. Campbell, M. M.; Kaye, A. D.; Sainsbury, M.; Yavarzadeh, R. Tetrahedron 1984, 40, 2461;
26. Campbell, M. M.; Sainsbury, M.; Yavarzadeh, R. Tetrahedron Ibid. 1984, 40, 5063;
27. Ogawa, S., Yato, Y.; Nakamura, K.; Takata, M.; Takagaki, T. Carbohydr. Res. 1986, 148, 249;
28. Ogawa, S.; Uemura, M.; Fujita, T. Carbohydr. Res. Ibid. 1988, 177, 213;
29. Koreeda, M.; Jung, K.-Y.; Ichita, J. J. Chem. Soc., Perkin Trans I, 1989, 2129;
30. Suami, T. Top. Curr. Chem. 1990, 154, 257;
31. Takahashi, T.; Kotsubo, H.; Iyobe, A.; Namiki, T.; Koizumi, T. J. Chem. Soc., Perkin Trans I 1990, 3065;
32. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173;
33. Reynard, E., Reymond, J.-L.; Vogel, P. Synlett 1991, 469;
34. Ogawa, S., Tsunoda, H.; Yoshikawa, M.; Uemura, M.; Orihara, M. Liebigs Ann. Chem. 1992, 629;
35. Aceña, J. L.; Arjona, O.; Fernandez de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1992, 57, 1945;
36. Aceña, J. L.; Arjona, O.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 6419;
37. Aceña, J. L.; Arjona, O.; Iradier, F.; Plumet, J. Tetrahedron Lett. 1996, 37, 105.
38. Theurillat-Moritz, V.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 3163.
39. Yadav, J. S., Renduchintala, R.; Samala, L. Tetrahedron Lett. 1994, 35, 3617.
40. Brown, G. M.; Dubreuil, P. Can. J. Chem. 1963, 46, 1577.
41. Koreeda, M.; Jung, K.-J.; Hirota, M. J. Am. Chem. Soc. 1990, 112, 7413.
42. 3J=6.8), 4.07 (m, H-1), 2.61 (m, H-5), 2.33 (m, H-6), 2.48 (br. s, OH), 2.10, 2.08 & 2.05 (3s, 3Me).
43. 1H-NMR spectra. Details will be given in a forthcoming full paper.
44. Papa, A. J. J.Org.Chem. 1966, 2, 1426.
45. C: 171.2, 170.4, 170.3 (3s), 138.5 (s), 121.8, 69.0 (2d), 65.5, 63.5, 62.3 (3t), 60.3, 37.8, 36.4 (3d), 20.9, 20.83, 20.81 (3q).
46. C: 139.9 (s), 125.0, 70.2 (2d), 63.8, 60.7, 58.0 (3t), 51.8, 39.7, 37.8 (3d).
47. C: 158.1, 142.6, 138.3 (3s), 129.5, 129.0, 128.9, 122.9, 69.3 (4d), 67.5, 64.9, 62.0, 58.3 (40, 53.4, 41.1, 38.5 (3d).
48. Shing, K. M. T.; Tam, K. W. E.; Tai, W. F. V.; Chung, H. F. I.; Jiang, Q. Chem. Eur. J. 1996, 2, 50.
49. C: 171.3, 171.2, 170.9, 73.90 (4s), 72.4, 72.2, 65.4 (3d), 62.8, 61.7, 61.5 (3dd), 40.7, 37.9 (2d), 21.1, 20.8 (3q).
50. 3J=8.5, 5.6, H-6).
51. C: 138.1 (s), 123.7, 68.5 (2d), 61.9 (t), 60.4 (d), 58.2, 54.9 (2t), 39.9, 39.0 (2d).
52. 1J(C,H)=156), 72.6 (d, 147), 61.7 (t, 139), 59.1 (t, 143), 53.6 (d, 137), 46.0 (t, 129), 41.7, 40.7 (2d, 125).
53. Demange, R.; Vogel, P. unpublished.