Nitrone cycloadditions to isolevoglucosenone: Ready access to a new class of directly linked (1→3)-imino-C-disaccharides

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1475-1478

  Cardona, Francesca ^a   Goti, Andrea ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUND; DISACCHARIDE; ISOLEVOGLUCOSENONE; NITRONE; OXIDE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; 1,6 ANHYDRO 2,3 DIDEOXYHEX 3 ENOPYRAN 4 ULOSE; 1,6-ANHYDRO-2,3-DIDEOXYHEX-3-ENOPYRAN-4-ULOSE; FUSED HETEROCYCLIC RINGS; NITROGEN OXIDE; NITRONES; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CYCLOADDITION; DERIVATIZATION; DRUG SYNTHESIS; HYDROXYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CARBOHYDRATE CONFORMATION; CYCLIZATION; DISACCHARIDES; NITROGEN OXIDES; PYRROLES; STEREOISOMERISM;

EID: 0042766862     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0342507     Document Type: Article

References (46)

1. Iminosugars as Glycosidase Inhibitors. Nojirimycin and Beyond; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999.
2. See, e.g.: (a) Horii, S.; Fukase, H.; Matsuo, T.; Kameda, Y.; Asano, N.; Matsui, K. J. Med. Chem. 1986, 29, 1038-1046. (b) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497-594.
3. See, e.g.: (a) Horii, S.; Fukase, H.; Matsuo, T.; Kameda, Y.; Asano, N.; Matsui, K. J. Med. Chem. 1986, 29, 1038-1046. (b) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497-594.
4. See, e.g.: (a) Karlsson, G. B.; Butters, T. D.; Dwek, R. A.; Platt, F. M. J. Biol. Chem. 1993, 268, 570-576. (b) Fenouillet, E.; Papandreou, M.-J.; Jones, I. M. Virology 1997, 231, 89-95.
5. See, e.g.: (a) Karlsson, G. B.; Butters, T. D.; Dwek, R. A.; Platt, F. M. J. Biol. Chem. 1993, 268, 570-576. (b) Fenouillet, E.; Papandreou, M.-J.; Jones, I. M. Virology 1997, 231, 89-95.
6. See, e.g.: (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215-5222. (b) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450-1457.
7. See, e.g.: (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215-5222. (b) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450-1457.
8. (a) Legler, G. In Carbohydrate Mimics; Chapleur, Y., Ed; Wiley-VCH: Weinheim, Germany, 1998; pp 461-490.
9. (b) Martin, O. R. In Carbohydrate Mimics. Concepts and Methods; Chapleur, Y., Ed; Wiley-VCH: Weinheim, Germany, 1998; p 259.
10. (a) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991-8994.
11. (b) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991-1994.
12. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R. J. Am. Chem. Soc. 1997, 119, 4856-4865.
13. (d) Leeuwenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; van der Marel, G. A.; Vogel, P.; van Boom, J. H. Eur. J. Org. Chem. 1999, 1185, 5-1189.
14. (e) Duff, F. J.; Vivien, V.; Wightman, R. H. Chem. Commun. 2000, 2127-2128.
15. (f) Dondoni, A.; Giovannini, P. P.; Perrone, D. J. Org. Chem. 2002, 67, 7203-7214.
16. (a) Frérot, E.; Marquis, C. Vogel, P. Tetrahedron Lett. 1996, 37, 2023-2026.
17. (b) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483-484.
18. (c) Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252-6260.
19. (d) Kraehenbuehl, K.; Picasso, S.; Vogel, P. Helv. Chim. Acta 1998, 81, 1439-1479.
20. (e) Zhu, Y.-H.; Vogel, P. Chem. Commun. 1999, 1873-1874.
21. (f) Marquis, C.; Picasso, S.; Vogel, P. Synthesis 1999, 1441-1452.
22. (g) Zhu, Y.-H.; Vogel, P. J. Org. Chem. 1999, 64, 666-669.
23. (h) Cheng, X.; Kumaran, G.; Mootoo, D. R. Chem. Commun. 2001, 811-812.
24. (i) Navarro, I.; Vogel. P. Helv. Chim. Acta 2002, 85, 152-160.
25. (a) Cardona, F.; Robina, I.; Vogel, P. J. Carbohydr. Chem. 2000, 19, 555-571.
26. (b) Marquis, C.; Cardona, F.; Robina, I.; Wurth, G.; Vogel, P. Heterocycles 2002, 56, 181-208.
27. Cardona, F.; Valenza, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1997, 38, 8097-8100.
28. Cardona, F.; Valenza, S.; Picasso, S.; Goti, A.; Brandi, A. J. Org. Chem. 1998, 63, 7311-7318.
29. Cardona, F.; Salanski, P.; Chmielewski, M.; Valenza, S.; Goti, A.; Brandi, A. Synlett 1998, 1444-1446.
30. For recently reported cycloadditions of nitrones 4 to sugar-derived α, β-unsaturated lactones, see: (a) Jurczak, M.; Rabiczko, J.; Socha, D.; Chmielewski, M.; Cardona, F.; Goti, A.; Brandi, A. Tetrahedron: Asymmetry 2000, 11, 2015-2022. (b) Socha, D.; Jurczak, M.; Frelek, J.; Klimek, A.; Rabiczko, J.; Urbańczyk-Lipkowska, Z.; Suwińska, K.; Chmielewski, M.; Cardona, F.; Goti, A.; Brandi, A. Tetrahedron: Asymmetry 2001, 12, 3163-3172.
31. For recently reported cycloadditions of nitrones 4 to sugar-derived α, β-unsaturated lactones, see: (a) Jurczak, M.; Rabiczko, J.; Socha, D.; Chmielewski, M.; Cardona, F.; Goti, A.; Brandi, A. Tetrahedron: Asymmetry 2000, 11, 2015-2022. (b) Socha, D.; Jurczak, M.; Frelek, J.; Klimek, A.; Rabiczko, J.; Urbańczyk-Lipkowska, Z.; Suwińska, K.; Chmielewski, M.; Cardona, F.; Goti, A.; Brandi, A. Tetrahedron: Asymmetry 2001, 12, 3163-3172.
32. Levoglucosenone and Levoglucosans, Chemistry and Applications; Witczak, Z. J., Ed.; ALT Press, Inc., Science Publishers: Mount Prospect, IL, 1994.
33. (a) Blake, A. J.; Forsyth, A. C.; Paton, R. M. J. Chem. Soc., Chem. Commun, 1988, 440-442.
34. (b) Blake, A. J.; Cook, T. A.; Forsyth, A. C.; Gould, R. O.; Paton, R. M. Tetrahedron 1992, 48, 8053-8064.
35. Horton, D.; Norris, P.; Roski, J. J. Org. Chem. 1996, 61, 3783-3793.
36. For more recent syntheses of 7, see: (a) Witczak, Z. J.; Chen, H.; Kaplon, P. Tetrahedron: Asymmetry 2000, 11, 519-532. (b) Kadota, K.; ElAzab, A. S.; Taniguchi, T.; Ogasawara, K. Synthesis 2000, 1372-1374. (c) Witczak, Z. J.; Kaplon, P.; Kolodziej, M. J. Carbohydr. Chem. 2002, 21, 143-148.
37. For more recent syntheses of 7, see: (a) Witczak, Z. J.; Chen, H.; Kaplon, P. Tetrahedron: Asymmetry 2000, 11, 519-532. (b) Kadota, K.; ElAzab, A. S.; Taniguchi, T.; Ogasawara, K. Synthesis 2000, 1372-1374. (c) Witczak, Z. J.; Kaplon, P.; Kolodziej, M. J. Carbohydr. Chem. 2002, 21, 143-148.
38. For more recent syntheses of 7, see: (a) Witczak, Z. J.; Chen, H.; Kaplon, P. Tetrahedron: Asymmetry 2000, 11, 519-532. (b) Kadota, K.; ElAzab, A. S.; Taniguchi, T.; Ogasawara, K. Synthesis 2000, 1372-1374. (c) Witczak, Z. J.; Kaplon, P.; Kolodziej, M. J. Carbohydr. Chem. 2002, 21, 143-148.
39. Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem. 1993, 58, 5274-5275.
40. Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem. 1995, 60, 4743-4748.
41. For an account on kinetic resolutions by means of cycloaddition reactions, see: Cardona, F.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 2001, 2999-3011.
42. Goti, A.; Cicchi, S.; Cacciarini, M.; Cardona, F.; Fedi, V.; Brandi, A. Eur. J. Org. Chem. 2000, 3633-3645.
43. By means of cycloadditions to triacetyl-D-glucal, (3S,4R)-nitrone 15 could be recovered with 37% ee: Cardona, F.; Valenza, S.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 1999, 1319-1323.
44. 3 as a chiral shift reagent: Cicchi, S.; Corsi, M.; Brandi, A.; Goti, A. J. Org. Chem. 2002, 67, 1678-1681.
45. Witczak, Z. J.; Chhabra, R.; Chen, H.; Xie, X.-Q. Carbohydr. Res. 1997, 301, 167-175.
46. Chen, X.-Y.; Link, T. M.; Schramm, V. L. J. Am. Chem. Soc. 1996, 118, 3067-3068.