D-gulonolactone as a synthon for L-noviose: First preparation of 4-O-demethyl-L-noviofuranose and related derivatives

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2651-2653

  Ješelnik, Marjan ^a   Leban, Ivan ^a   Polanc, Slovenko ^a   Kočevar, Marijan ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

4 O NOR LEVO NOVIOFURANOSE; 7 [1 O BENZYLMETHYL 2,3 O (1 METHYLETHYLIDENE) ALPHA LEVO LYXOFURANOSIDURONATE]; DEXTRO GULONOLACTONE; ESTER DERIVATIVE; FURAN DERIVATIVE; LACTONE DERIVATIVE; LEVO NOVIOSE; NOVOBIOCIN; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

FURANS; MODELS, MOLECULAR; NOVOBIOCIN; PENTOSES; STEREOISOMERISM; SUGAR ACIDS;

EID: 0141631564     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034796t     Document Type: Article

References (39)

1. Drlica, K.; Franco, R. J. Biochemistry 1988, 27, 2253.
2. Gormley, N. A.; Orphanides, G.; Meyer, A.; Cullis, P. M.; Maxwell, A. Biochemistry 1996, 35, 5083.
3. (a) Wigley, D. B.; Davies, G. J.; Dodson, E. J.; Maxwell, A. Nature 1991, 351, 624.
4. (b) Hockings, S. C.; Maxwell, A. J. Mol. Biol. 2002, 318, 351.
5. Zhang, M. Q.; Haemers, A. Pharmazie 1991, 46, 687.
6. Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Skarzynski, T.; Maxwell, A. ; Wonacott, A. J.; Wigley, D. B. EMBO J. 1996, 15, 1412.
7. (a) Ueda, Y.; Chuang, J. M.; Crast, L. B.; Partyka, R. A. J. Org. Chem. 1988, 53, 5107.
8. (b) Ueda, Y.; Chuang, J. M.; Crast, L. B., Jr.; Partyka, R. A. J. Antibiot. 1989, 42, 1379.
9. (c) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J.; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623.
10. (a) Bell, W.; Block, M. H.; Cook, C.; Grant, J. A.; Timms, D.J. Chem. Soc., Perkin Trans. 1 1997, 2789.
11. (b) Laurin, P.; Ferroud, D.; Schio, L.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2875.
12. (c) Ferroud, D.; Collard, J.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P. ; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2881.
13. (d) Periers, A.-M.; Laurin, P.; Ferroud, D.; Haesslein, J.-L.; Klich, M. ; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 2000, 10, 161.
14. (e) Musicki, B.; Periers, A.-M.; Laurin, P.; Ferroud, D.; Benedetti, Y.; Lachaud, S.; Chatreaux, F.; Haesslein, J.-L.; Iltis, A.; Pierre, C.; Khider, J. ; Tessot, N.; Airault, M.; Demassey, J.; Dupuis-Hamelin, C.; Lassaigne, P.; Bonnefoy, A.; Vicat, P.; Klich, M. Bioorg. Med. Chem. Lett. 2000, 10, 1695.
15. (f) Schio, L.; Chatreaux, F.; Klich, M. Tetrahedron Lett. 2000, 41, 1543.
16. (g) Peixoto, C.; Laurin, P.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Tetrahedron Lett. 2000, 41, 1741.
17. (h) Boehm, H.-J.; Boehringer, M.; Bur, D.; Gmuender, H.; Huber, W.; Klaus, W.; Kostrewa, D.; Kuehne, H.; Luebbers, T.; Meunier-Keller, N.; Mueller, F. J. Med. Chem. 2000, 43, 2664.
18. (i) Schio, L.; Chatreaux, F.; Loyau, V.; Murer, M.; Ferreira, A.; Mauvais, P.; Bonnefoy, A.; Klich, M. Bioorg. Med. Chem. Lett. 2001, 11, 1461.
19. (j) Olson, S. H.; Slossberg, L. H. Tetrahedron Lett. 2003, 44, 61.
20. Ješelnik, M.; Plavec, J.; Polanc, S.; Kočevar, M. Carbohydr. Res. 2000, 328, 591.
21. Arnone, A.; Nasini, G.; Cavalleri, B. J. Chem. Soc., Perkin Trans. 1 1987, 1353.
22. (a) Vaterlaus, B. P.; Doebel, K.; Kiss, J.; Rachlin, A. I.; Spiegelberg, H. Experientia 1963, 19, 383.
23. (b) Vaterlaus, B. P.; Doebel, K.; Kiss, J.; Rachlin, A. I.; Spiegelberg, H. Helv. Chim. Acta 1964, 47, 390.
24. (c) Vaterlaus, B. P.; Spiegelberg, H. Helv. Chim. Acta 1964, 47, 508.
25. (a) Laurin, P.; Ferroud, D.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079.
26. (b) Periers, A.-M.; Laurin, P.; Benedetti, Y., Lachaud, S.; Ferroud, D.; Iltis, A.; Haesslein, J.-L.; Klich, M.; L'Hermite, G.; Musicki, B. Tetrahedron Lett. 2000, 41, 867.
27. Klemer, A.; Waldmann, M. Liebigs Ann. Chem. 1986, 221.
28. Gammon, D. W.; Hunter, R.: Wilson, S. Tetrahedron Lett. 2002, 43, 3141.
29. Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 2609.
30. Achmatowicz, O., Jr.; Grynkiewicz, G.; Szechner, B. Tetrahedron 1976, 32, 1051.
31. (a) Buchanan, J. G.; Moorhouse, S. J.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1981, 2258.
32. (b) Ireland, R. E.; Vevert, J.-P. Can. J. Chem. 1981, 59, 572.
33. (c) Rosen, T.; Taschner, M. J.; Heathcock, C. H. J. Org. Chem. 1984, 49, 3994.
34. (a) Hudlický, M. Oxidations in Organic Chemistry; ACS Monograph 186; Washington, DC, 1990.
35. (b) Ireland, R. E.; Norbeck, D. W. J. Am. Chem. Soc. 1985, 107, 3279.
36. Arndt, F.; Noller, C. R.; Bergsteinsson, I. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, p 165.
37. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; J. Wiley & Sons, Inc.: New York, 1999.
38. (b) Kocieñski, P. J. Protecting Groups; Georg Thieme Verlag: Stuttgart, Corrected ed. 2000.
39. Unpublished results.