Total synthesis of new C-6 homologues of 1-deoxynojirimycin and 1-deoxy- L-idonojirimycin

Chemical Communications

Volumn , Issue 6, 2000, Pages 471-472

  Szolcsányi, Peter ^a   Gracza, Tibor ^a   Koman, Marian ^a   Prónayová, Naïa ^a   Liptaj, Tibor ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXY LEVO IDONOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034696656     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908449e     Document Type: Article

References (24)

1. B. Winchester and G. W. J. Fleet, J. Glycobiol., 1992, 2, 199; M. L. Sinnot, Chem. Rev., 1990, 90, 1171.
2. B. Winchester and G. W. J. Fleet, J. Glycobiol., 1992, 2, 199; M. L. Sinnot, Chem. Rev., 1990, 90, 1171.
3. E. Truscheit, W. Frommer, B. Junge, L. Müller, D. D. Schmidt and W. Wingender, Angew. Chem., Int. Ed. Engl., 1981, 20, 744.
4. M. J. Humphries, K. Matsumoto and S. L. White, Cancer Res., 1986, 46, 5215.
5. A. Karpas, G. W. J. Fleet, R. A. Dwek, S. Petursson, S. K. Namgoong, N. G. Ramsden, G. S. Jacob and T. W. Rademacher, Proc. Natl. Acad. Sci. U.S.A., 1988, 85, 9229.
6. I. Lundt and R. Madsen, Synthesis, 1995, 787; C. Herdeis and T. Schiffer, Tetrahedron, 1996, 52, 14 745.
7. I. Lundt and R. Madsen, Synthesis, 1995, 787; C. Herdeis and T. Schiffer, Tetrahedron, 1996, 52, 14 745.
8. G. Rassu, L. Pinna, N. Culeddu, G. Casiraghi, G. Gasparri Fava, M. Belicchi Ferrari and G. Pelosi, Tetrahedron, 1992, 48, 727; J. P. Shilvock, K. Y. Hsia, R. J. Nash, J. D. Lloyd, A. L. Winters, N. Asano and G. W. J. Fleet, Tetrahedron: Asymmetry, 1998, 9, 4157.
9. G. Rassu, L. Pinna, N. Culeddu, G. Casiraghi, G. Gasparri Fava, M. Belicchi Ferrari and G. Pelosi, Tetrahedron, 1992, 48, 727; J. P. Shilvock, K. Y. Hsia, R. J. Nash, J. D. Lloyd, A. L. Winters, N. Asano and G. W. J. Fleet, Tetrahedron: Asymmetry, 1998, 9, 4157.
10. Y. Chen and P. Vogel, J. Org. Chem., 1994, 59, 2487; S. Picasso, Y. Chen and P. Vogel, Carbohydr. Lett., 1994, 1, 1; A. Baudat, S. Picasso and P. Vogel, Carbohydr. Res., 1996, 281, 277.
11. Y. Chen and P. Vogel, J. Org. Chem., 1994, 59, 2487; S. Picasso, Y. Chen and P. Vogel, Carbohydr. Lett., 1994, 1, 1; A. Baudat, S. Picasso and P. Vogel, Carbohydr. Res., 1996, 281, 277.
12. Y. Chen and P. Vogel, J. Org. Chem., 1994, 59, 2487; S. Picasso, Y. Chen and P. Vogel, Carbohydr. Lett., 1994, 1, 1; A. Baudat, S. Picasso and P. Vogel, Carbohydr. Res., 1996, 281, 277.
13. A. Kilonda, F. Compernolle, S. Toppet and G. J. Hoornaert, Tetrahedron Lett., 1994, 35, 9047; F. Compernolle, G. Joly, K. Peeters, S. Toppet, G. J. Hoornaert, A. Kilonda and B. Babady, Tetrahedron, 1997, 53, 12 739.
14. A. Kilonda, F. Compernolle, S. Toppet and G. J. Hoornaert, Tetrahedron Lett., 1994, 35, 9047; F. Compernolle, G. Joly, K. Peeters, S. Toppet, G. J. Hoornaert, A. Kilonda and B. Babady, Tetrahedron, 1997, 53, 12 739.
15. Y. Tamaru, T. Kobayashi, S. Kawamura, H. Ochiai and Z. Yoshida, Tetrahedron Lett., 1985, 26, 4479; Y. Tamaru and Z. Yoshida, J. Organomet. Chem., 1987, 334, 213; W. Hümmer, E. Dubois, T. Gracza and V. Jäger, Synthesis, 1997, 634.
16. Y. Tamaru, T. Kobayashi, S. Kawamura, H. Ochiai and Z. Yoshida, Tetrahedron Lett., 1985, 26, 4479; Y. Tamaru and Z. Yoshida, J. Organomet. Chem., 1987, 334, 213; W. Hümmer, E. Dubois, T. Gracza and V. Jäger, Synthesis, 1997, 634.
17. Y. Tamaru, T. Kobayashi, S. Kawamura, H. Ochiai and Z. Yoshida, Tetrahedron Lett., 1985, 26, 4479; Y. Tamaru and Z. Yoshida, J. Organomet. Chem., 1987, 334, 213; W. Hümmer, E. Dubois, T. Gracza and V. Jäger, Synthesis, 1997, 634.
18. V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, U. Kautz, B. Kirschbaum, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl and O. Stephan, Pd(II)-Catalyzed Carbonylation of Unsaturated Polyols and Aminopolyols, in Organic Synthesis via Organometallics OSM 5, Vieweg, Germany, 1997, p. 331.
19. (a) Y. Tamaru, M. Hojo and Z. Yoshida, J. Org. Chem., 1988, 53, 5731;
20. (b) Y. Tamaru and M. Kimura, Synlett, 1997, 749.
21. R. C. Bernotas, M. A. Pezzone and B. Ganem, Carbohydr. Res., 1987, 167, 305; R. C. Bernotas, Tetrahedron Lett., 1990, 31, 469.
22. R. C. Bernotas, M. A. Pezzone and B. Ganem, Carbohydr. Res., 1987, 167, 305; R. C. Bernotas, Tetrahedron Lett., 1990, 31, 469.
23. T. Morie and S. Kato, Heterocycles, 1998, 48, 427.
24. M. Koman, P. Szolcsányi and T. Gracza, submitted for publication.