Synthesis of iminosugars from α,β-unsaturated lactones and N-benzyl nitrone

Polish Journal of Chemistry

Volumn 79, Issue 2, 2005, Pages 239-249

  Panfil, I ^a   Urbanczyk Lipkowska Z ^a   Chmielewski, M ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

1,3 dipolar cycloaddition; Iminosugars; Unsaturated aldono 1,5 lactones

Indexed keywords

CARBOHYDRATE DERIVATIVE; LACTONE DERIVATIVE; NITROGEN; NITRONE DERIVATIVE; OXYGEN;

ALKYLATION; ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; HYDROGENOLYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 15744368754     PISSN: 01375083     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. Zamojski A., Banaszek A. and Grynkiewicz G., Advances Carbohydr. Chem. Biochem., 40,1 (1982); Zamojski A. and Gtynkiewicz G., in The Total Synthesis of Natural Products, ApSimon J. Ed.; Wiley, New York, 1984, Vol. 6, p. 41.
2. Zamojski A., Banaszek A. and Grynkiewicz G., Advances Carbohydr. Chem. Biochem., 40,1 (1982); Zamojski A. and Gtynkiewicz G., in The Total Synthesis of Natural Products, ApSimon J. Ed.; Wiley, New York, 1984, Vol. 6, p. 41.
3. Mieczkowski J., Jurczak J., Chmielewski M. and Zamojski A., Carbohydr. Res., 56, 180 (1977).
4. Chmielewski M., Jurczak J. and Maciejewski S., Carbohydr. Res., 165, 111 (1987).
5. Hamann H.-J., Hoft E., Mostowicz D., Mishnev A., Urbańczyk- Lipkowska Z. and Chmielewski M., Tetrahedron, 53, 185 (1987).
6. Mostowicz D., Jurczak M., Hamann H.-J., Hoft E. and Chmielewski M., Eur. J. Org. Chem., 2617 (1998).
7. Jarglis P. and Lichtenthaler F.W., Tetrahedron Lett., 23, 3781 (1982); Jarglis P., Ronninger S. and Lichtenthaler F.W., Liebigs. Chem., 1153 (1989).
8. Jarglis P. and Lichtenthaler F.W., Tetrahedron Lett., 23, 3781 (1982); Jarglis P., Ronninger S. and Lichtenthaler F.W., Liebigs. Chem., 1153 (1989).
9. Rabiczko J., Urbańczyk-Lipkowska Z. and Chmielewski M., Tetrahedron, 58, 1433 (2002).
10. Socha D., Jurczak M. and Chmielewski M., Carbohydr. Res. 336, 315 (2001).
11. Socha D., Jurczak M. and Chmielewski M., Tetrahedron, 53, 739 (1997).
12. Jurczak M., Mostowicz D., Panfil I., Rabiczko J., Socha D. and Chmielewski M., in Targets in Heterocyclic Systems, Attanasi, O., Ed.; Springer: Berlin, 2001; Vol. 5, p. 59.
13. Fleet G.W.J., Fellows L.E. and Winchester B., in Bioactive Compounds from Plants, Eds: Chadwick P.J. and March J., Wiley&Sons, Chichester 1990, p. 112; Asano N., Nash R.J., Molyneux R.J. and Fleet G.W.J., Tetrahedron: Asymmetry, 11, 1645 (2000).
14. Fleet G.W.J., Fellows L.E. and Winchester B., in Bioactive Compounds from Plants, Eds: Chadwick P.J. and March J., Wiley&Sons, Chichester 1990, p. 112; Asano N., Nash R.J., Molyneux R.J. and Fleet G.W.J., Tetrahedron: Asymmetry, 11, 1645 (2000).
15. Chapleur Y., Ed., Carbohydrate Mimics, Wiley-VCH, Weinheim, 1998.
16. Stutz A.E., Iminosugars as Glycosidase Inhibitors, Wiley-VCh, Weinheim 1999.
17. Martin O.R. and Compain Ph., Eds, Current Topics in Medicinal Chemistry, 3, issue 5 (2003) and references cited therein.
18. El Nemr A., Tetrahedron, 56, 8579 (2000); Felpin F.-X. and Lebreton J., Eur. J. Chem., 3693 (2003); Cossy J. and Vogel P., in Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1993, p. 275.
19. El Nemr A., Tetrahedron, 56, 8579 (2000); Felpin F.-X. and Lebreton J., Eur. J. Chem., 3693 (2003); Cossy J. and Vogel P., in Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1993, p. 275.
20. El Nemr A., Tetrahedron, 56, 8579 (2000); Felpin F.-X. and Lebreton J., Eur. J. Chem., 3693 (2003); Cossy J. and Vogel P., in Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier, Amsterdam, 1993, p. 275.
21. Herczegh P., Kovacs I. and Sztaricskai F., Recent Progress in Chemical Synthesis of Antibiotics, Lukacs, G. and Ohno M., Eds; Springer-Verlag: Berlin, 1993, p. 751; Felpin F.-X. and Lebreton J., Eur. J. Org. Chem., 3693 (2003).
22. Herczegh P., Kovacs I. and Sztaricskai F., Recent Progress in Chemical Synthesis of Antibiotics, Lukacs, G. and Ohno M., Eds; Springer-Verlag: Berlin, 1993, p. 751; Felpin F.-X. and Lebreton J., Eur. J. Org. Chem., 3693 (2003).
23. Cipolla L., La Ferla B. and Nicotra F., Current Topics in Medicinal Chemistry, 3, 485 (2003).
24. Cardona F., Goti A., Picasso S., Vogel P. and Brandi A., J. Carbohydr. Chem., 19, 585 (2000). McCaig A.E., Meldrum K.P. and Wightman R.H., Tetrahedron, 54, 9429 (1998).
25. Cardona F., Goti A., Picasso S., Vogel P. and Brandi A., J. Carbohydr. Chem., 19, 585 (2000). McCaig A.E., Meldrum K.P. and Wightman R.H., Tetrahedron, 54, 9429 (1998).
26. Bartnicka E. and Zamojski A., Tetrahedron, 55, 2061 (1999).
27. Panfil I. and Chmielewski M., Tetrahedron, 41, 4713 (1985).
28. Panfil I., Bełzecki C., Urbańczyk-Lipkowska Z. and Chmielewski M., Tetrahedron, 47, 10087 (1991).
29. Greimel P., Spreitz J., Stutz A.E. and Wrodnigg T.M., Current Topics in Medicinal Chemistry, 3, 513 (2003); Compain Ph. and Martin O.R., Current Topics in Medicinal Chemistry, 3, 541 (2003); Butters T.D., Dwek R.A. and Platt F.M., Current Topics in Medicinal Chemistry, 3, 561 (2003); Asano N., Nishida M., Kato A., Kizu H., Matsui K., Shimada Y., Watson A.A., Nash R.J., de Q. Lilley P.M., Itoh T., Baba M. and Fleet G.W.J., J. Med. Chem., 41, 2565 (1998).
30. Greimel P., Spreitz J., Stutz A.E. and Wrodnigg T.M., Current Topics in Medicinal Chemistry, 3, 513 (2003); Compain Ph. and Martin O.R., Current Topics in Medicinal Chemistry, 3, 541 (2003); Butters T.D., Dwek R.A. and Platt F.M., Current Topics in Medicinal Chemistry, 3, 561 (2003); Asano N., Nishida M., Kato A., Kizu H., Matsui K., Shimada Y., Watson A.A., Nash R.J., de Q. Lilley P.M., Itoh T., Baba M. and Fleet G.W.J., J. Med. Chem., 41, 2565 (1998).
31. Greimel P., Spreitz J., Stutz A.E. and Wrodnigg T.M., Current Topics in Medicinal Chemistry, 3, 513 (2003); Compain Ph. and Martin O.R., Current Topics in Medicinal Chemistry, 3, 541 (2003); Butters T.D., Dwek R.A. and Platt F.M., Current Topics in Medicinal Chemistry, 3, 561 (2003); Asano N., Nishida M., Kato A., Kizu H., Matsui K., Shimada Y., Watson A.A., Nash R.J., de Q. Lilley P.M., Itoh T., Baba M. and Fleet G.W.J., J. Med. Chem., 41, 2565 (1998).
32. Greimel P., Spreitz J., Stutz A.E. and Wrodnigg T.M., Current Topics in Medicinal Chemistry, 3, 513 (2003); Compain Ph. and Martin O.R., Current Topics in Medicinal Chemistry, 3, 541 (2003); Butters T.D., Dwek R.A. and Platt F.M., Current Topics in Medicinal Chemistry, 3, 561 (2003); Asano N., Nishida M., Kato A., Kizu H., Matsui K., Shimada Y., Watson A.A., Nash R.J., de Q. Lilley P.M., Itoh T., Baba M. and Fleet G.W.J., J. Med. Chem., 41, 2565 (1998).
33. Jakobsen P., Lundbeck J.M., Kristiansen M., Breinholt J., Demuth H., Pawlas J., Torres Candela M.P., Andersen B., Westergaard N., Lundgren K. and Asano N., Bioorg. Med. Chem., 9, 733 (2001).
34. Cicchi S., Hold I. and Brandi A., J. Org. Chem., 58, 5274 (1993); Ballini R., Marcantoni E. and Petrini M., J. Org. Chem., 57, 1316 (1992).
35. Cicchi S., Hold I. and Brandi A., J. Org. Chem., 58, 5274 (1993); Ballini R., Marcantoni E. and Petrini M., J. Org. Chem., 57, 1316 (1992).
36. Cicchi S., Goti A. and Brandi A., J. Org. Chem., 60, 4743 (1995).
37. Jurczak M., Rabiczko J., Socha D., Chmielewski M., Cardona F., Goti A. and Brandi A., Tetrahedron: Asymmetry, 11, 2015 (2000); Socha D., Jurczak M., Frelek F., Klimek A., Rabiczko J., Urbańczyk-Lipkowska Z., Suwińska K., Chmielewski M., Cardona F., Goti A. and Brandi A., Tetrahedron: Asymmetry, 12, 3163 (2001); Pasniczek K., Socha D., Jurczak M., Frelek J., Suszczyńska A., Urbańczyk-Lipkowska Z. and Chmielewski M., J. Carbohydr. Chem., 22, 613 (2003).
38. Jurczak M., Rabiczko J., Socha D., Chmielewski M., Cardona F., Goti A. and Brandi A., Tetrahedron: Asymmetry, 11, 2015 (2000); Socha D., Jurczak M., Frelek F., Klimek A., Rabiczko J., Urbańczyk-Lipkowska Z., Suwińska K., Chmielewski M., Cardona F., Goti A. and Brandi A., Tetrahedron: Asymmetry, 12, 3163 (2001); Pasniczek K., Socha D., Jurczak M., Frelek J., Suszczyńska A., Urbańczyk-Lipkowska Z. and Chmielewski M., J. Carbohydr. Chem., 22, 613 (2003).
39. Jurczak M., Rabiczko J., Socha D., Chmielewski M., Cardona F., Goti A. and Brandi A., Tetrahedron: Asymmetry, 11, 2015 (2000); Socha D., Jurczak M., Frelek F., Klimek A., Rabiczko J., Urbańczyk-Lipkowska Z., Suwińska K., Chmielewski M., Cardona F., Goti A. and Brandi A., Tetrahedron: Asymmetry, 12, 3163 (2001); Pasniczek K., Socha D., Jurczak M., Frelek J., Suszczyńska A., Urbańczyk-Lipkowska Z. and Chmielewski M., J. Carbohydr. Chem., 22, 613 (2003).
40. Xiang Y., Gong Y. and Zhao K., Tetrahedron Lett., 17, 1395 (1996); Tronchet J.M. J., Criton M., Zsely M., Besomi P. and Barblat-Rey F., Carbohydr. Lett., 2, 205 (1996); Panfil I., Abramski W. and Chmielewski M., J. Carbohydr. Chem., 17, 1395 (1998).
41. Xiang Y., Gong Y. and Zhao K., Tetrahedron Lett., 17, 1395 (1996); Tronchet J.M. J., Criton M., Zsely M., Besomi P. and Barblat-Rey F., Carbohydr. Lett., 2, 205 (1996); Panfil I., Abramski W. and Chmielewski M., J. Carbohydr. Chem., 17, 1395 (1998).
42. Xiang Y., Gong Y. and Zhao K., Tetrahedron Lett., 17, 1395 (1996); Tronchet J.M. J., Criton M., Zsely M., Besomi P. and Barblat-Rey F., Carbohydr. Lett., 2, 205 (1996); Panfil I., Abramski W. and Chmielewski M., J. Carbohydr. Chem., 17, 1395 (1998).
43. Crystallographic data for 43 have been deposited with the Cambridge Crystallographic Data Center, Cambridge, UK as a supplementary publication CCDC 248515.