Synthesis of pyrrolidine-based imino sugars as glycosidase inhibitors

European Journal of Organic Chemistry

Volumn , Issue 33, 2007, Pages 5583-5589

  Doddi, Venkata Ramana ^a   Vankar, Yashwant D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Diastereospecific dihydroxylation; Regiospecific amination; Ring closing metathesis

Indexed keywords

EID: 36349029687     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700719     Document Type: Article

References (54)

1. a) R. A. Dwek, Chem. Rev. 1996, 96, 683;
2. b) H. Lis, N. Sharon, Eur. J. Biochem. 1993, 218, 1;
3. c) A. D. Elbein, Annu. Rev. Biochem. 1987, 56, 497;
4. d) R. Kornfeld, S. Kornfeld, Annu. Rev. Biochem. 1985, 54, 631;
5. e) T. A. Beyer, J. I. Rearick, J. C. Paulson, J.-P. Prieels, J. E. Sadler, R. L. Hill, J. Biol. Chem. 1979, 254, 12531.
6. a) V. H. Lillelund, H. H. Jensen, X. Liang, M. Bols, Chem. Rev. 2002, 102, 515;
7. b) N. Asano, R. J. Nash, R. J. Molyneux, G. W. J. Fleet, Tetrahedron: Asymmetry 2000, 11, 1645;
8. c) T. D. Butters, R. A. Dwek, F. M. Piatt, Chem. Rev. 2000, 100, 4683;
9. d) T. D. Heightmann, A. T. Vasella, Angew. Chem. Int. Ed. 1999, 38, 751;
10. e) A. Bercibar, C. Grandjean, A. Siriwardena, Chem. Rev. 1999, 99, 779;
11. f) K. Tatsuta, in Carbohydrate Mimics (Ed.: Y. Chapleur), Wiley-VCH, Weinheim, 1998, pp. 283-305, and references cited therein.
12. a) G. Cai, S. Salonikidis Petrus, J. Fei, W. Schwarz, R. Schülein, W. Reutter, H. Fan, FEBS Lett. 2005, 272, 1625;
13. b) K. Karaveg, A. Siriwardena, W. Tempel, Z.-J. Liu, J. Glushka, B.-C. Wang, K. W. Moremen, J. Biol. Chem. 2005, 280, 16197;
14. c) D. L. Zechel, S. G. Withers, Acc. Chem. Res. 2000, 33, 11;
15. d) B. Ganem, Acc. Chem. Res. 1996, 29, 340.
16. A. Kato, N. Kato, E. Kano, I. Adachi, K. Ikeda, L. Yu, T. Okamoto, Y. Banba, H. Ouchi, H. Takahata, N. Asano, J. Med. Chem. 2005, 48, 2036.
17. For review articles, see: a) C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. Int. Ed. Engl. 1995, 34, 412;
18. b) A. B. Hughes, A. J. Rudge, Nat. Prod. Rep. 1994, 11, 135;
19. c) H. Paulsen, K. Todt, Adv. Carbohydr. Chem. Biochem. 1968, 23, 115;
20. d) S. Picasso, Chimin 1996, 50, 648;
21. e) L. A. G. M. van den Broek, Carbohydrates in Drug Design (Eds.: Z. J. Witczak, K. A. Nieforth), Dekker, New York, 1997, pp. 471;
22. f) Z. J. Witczak, in Carbohydrate Drug Res. (Eds.: Z. J. Witczak, K. A. Nieforth), Dekker, New York, 1997, pp. 1-37.
23. A. T. Carmona, J. Fuentes, I. Robina, J. Org. Chem. 2003, 68, 3874 and references cited therein.
24. Recent approaches for pyrrolidine-based azasugars a) S. Cren, C. Wilson, N. R. Thomas, Org. Lett. 2005, 7, 3521;
25. b) M. L. Ulf, D. Rui, H. Olle, Chem. Commun. 2005, 13, 1773;
26. c) T. Ayad, Y. Genisson, S. Broussy, M. Baltas, L. Gorrichon, Eur. J. Org. Chem. 2003, 15, 2903;
27. d) A. T. Carmona, J. Fuentes, I. Robina, G. E. Rodriguez, D. Raynald, P. Vogel, A. L. Winters, J. Org. Chem. 2003, 68, 3874;
28. e) T. J. Donohoe, C. E. Headley, R. P. C. Cousins, A. Cowley, Org. Lett. 2003, 5, 999.
29. a) G. W. J. Fleet, J. C. Son, D. S. Green, I. Cenci di Bello, B. Winchester, Tetrahedron 1988, 44, 2649;
30. b) S. Al Dasher, G. W. J. Fleet, S. K. Namgoong, B. Winchester, Biochem. J. 1989, 258, 613;
31. c) G. W. J. Fleet, J. C. Son, Tetrahedron 1988, 44, 2637;
32. d) G. W. J. Fleet, A. N. Shaw, S. V. Evans, L. E. Fellows, J. Chem. Soc. Chem. Commun. 1984, 1240;
33. e) G. Palamartczky, M. Mitchell, P. W. Smith, G. W. J. Fleet, A. D. Elbein, Arch. Biochem. Biophys. 1985, 242, 35;
34. f) I. Lundt, R. Madsen, Synthesis 1993, 720.
35. G. Masson, C. Philouze, P. Sandrine, Org. Biomol. Chem. 2005, 3, 2067 and references cited therein.
36. Y. Kameda, N. Asano, M. Yoshikawa, M. Takeuchi, T. Yamaguchi, K. Matsui, S. Horii, H. Fukase, J. Antibiot. 1984, 37, 1301.
37. H. Fukase, Yuki Gosei Kagaku Kyokaishi 1997, 55, 920.
38. a) M. Bols, M. P. Persson, W. M. Butt, M. Jorgensen, P. Christensen, L. T. Hansen, Tetrahedron Lett. 1996, 37, 2097;
39. b) M. Ichikawa, Y. Igarashi, Y. Ichikawa, Tetrahedron Lett. 1995, 36, 1767;
40. c) M. M. Matin, T. Sharma, S. G. Sabharwal, D. D. Dhavale, Org. Biomol. Chem. 2005, 3, 1702;
41. d) G. Pandey, M. Kapur, M. I. Khan, S. M. Gaikwad, Org. Biomol. Chem. 2003, 1, 3321;
42. e) A. Hansen, T. M. Tagmose, M. Bols, Tetrahedron 1997, 53, 697.
43. a) B. G. Reddy, Y. D. Vankar, Angew. Chem. Int. Ed. 2005, 44, 2001;
44. b) K. Jayakanthan, Y. D. Vankar, Org. Lett. 2005, 7, 5441;
45. c) K. Jayakanthan, Y. D. Vankar, Tetrahedron Lett. 2006, 49, 8667;
46. d) G. K. Rawal, S. Rani, A. Kumar, Y. D. Vankar, Tetrahedron Lett. 2006, 47, 9117.
47. C. R. Schmid, J. D. Bryant, M. Dowlatzedah, J. L. Phillips, D. E. Prather, R. D. Schantz, N. L. Sear, C. S. Vianco, J. Org. Chem. 1991, 56, 4056.
48. a) Y. Chengzhi, B. Liu, L. Hu, J. Org. Chem. 2001, 66, 5413;
49. b) P. R. Krishna, M. Narsingam, V. Kannan, Tetrahedron Lett. 2004, 45, 4773.
50. For details see the electronic supporting information.
51. S. Bergmeier, P. E. Seth, Tetrahedron Lett. 1999, 40, 6181.
52. Y.-T. Li, S.-C. Li, in Methods in Enzymology (Ed.: V. Ginsberg), Academic Press, 1972, pp. 702.
53. a) I. Lundt, R. Madsen, S. Al Daher, B. Winchester, Tetrahedron 1994, 50, 7513;
54. b) F. Popowycz, S. Gerber-Lemaire, R. Demange, E. Rodriguez-Garcia, A. T. C. Asenjo, I. Robina, P. Vogel, Bioorg. Med. Chem. Lett. 2001, 11, 2489.