Synthesis of calystegine B2 analogs by tandem tautomerization-intramolecular glycosylation of thioureidosugars

Synlett

Volumn , Issue 3, 1998, Pages 316-318

  Garcia Fernandez J M ^a   Ortiz Mellet, C ^b   Benito, J M ^a,b   Fuentes, J ^b  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000816726     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. The discovers of these compounds named them "calystegins". However, in recent literature the word is usually spelt "calystegines" because the extra "e" brings the name into line with most other alkaloids.
2. Tepfer, D.; Goldmann, A.; Pamboukdjian, N.; Maille, M.; Lepingle, A.; Chevalier, D.; Denarié, J.; Rosemberg, C. J. Bacteriol., 1988, 170, 1153.
3. Goldmann, A.; Message, B.; Tepfer, D.; Molineux, R. J.; Duclos, O.; Boyer, F.-D.; Pan, Y. T.; Elbein, A. D. J. Nat. Prod., 1996, 59, 1137.
4. Molineux, R. J.; Pan, Y. T.; Goldmann, A.; Tepfer, D. A.; Elbein, A. D. Arch. Biochem. Biophys., 1993, 304, 81.
5. Asano, N.; Oseki, K.; Tomioka, E.; Kizu, H.; Matsui, K. Carbohydr. Res., 1994, 259, 243.
6. Asano, N.; Kato, A.; Oseki, K.; Kizu, H.; Matsui, K. Eur. J. Biochem., 1995, 229, 369.
7. Asano, N.; Kato, A.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. Carbohydr. Res., 1996, 293, 195.
8. For recent reviews on glycosidase inhibitors and their uses see: Legier, G. Adv. Carbohydr. Chem. Biochem., 1990, 48, 319.
9. Sinnot, M. L. Chem. Rev., 1990, 90, 1171.
10. Nishimura, Y. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992, Vol. 10, p 495.
11. Kanshel, G. P.; Elbein, A. D. Methods Enzymol., 1994, 230, 316.
12. Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem., 1994, 37, 3701.
13. Ganem, B. Acc. Chem Res., 1996, 29, 340.
14. Boyer, F.-D.; Ducrot, P.-H.; Henryon, V.; Soulié, J.; Lallemand, J.-Y. Synlett, 1992, 357.
15. Boyer, F.-D.; Lallemand, J.-Y. Synlett, 1992, 969.
16. Duclos, O.; Duréault, A.; Depezay, J. C. Tetrahedron Lett., 1992, 33, 1059.
17. Duclos, O.; Mondange, M.; Duréault, A.; Depezay, J. C. Tetrahedron Lett., 1992, 33, 8061.
18. 2O.
19. Dax, K.; Gaigg, B.; Grassberger, V.; Kölblinger, B.; Stütz, A. E. J. Carbohydr. Chem. 1990, 9, 479.
20. García Fernández, J. M.; Ortiz Mellet, C.; Díaz Pérez, V. M., Jiménez Blanco, J. L.; Fuentes, J. Tetrahedron, 1996, 52, 12947.
21. Jiménez Blanco, J. L.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M. Chem. Commun., 1996, 2077.
22. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun., 1997, 1969.
23. Jefferies, I.; Bowen, B. R. Bioorg. Med. Chem. Lett. 1997, 7, 1171.
24. 2O) δ (ppm) = 57.7 (C-1), 71.2 (C-2), 76.1 (C-3), 74.3 (C-4), 88.0 (C-5), 65.9 (C-7), 84.1 (C-1′), 72.9 (C-2′), 77.0 (C-3′), 69.8 (C-4′), 68.7 (C-5′), 60.0 (C-6′), 179.2 (C=S).
25. For a recent review see: García Fernández, J. M.; Ortiz Mellet, C. Sulfur Rep., 1996, 19, 61.