J.-P. Praly et al. / Tetrahedron Letters 46(2005) 7081–7085
7085
1B.32,33 Complete synthetic results, including extension
of the syntheses to D-galacto configurated analogs, and
comparative biological evaluation will be reported in
due course.
8. Tai, A.; Goto, S.; Ishiguro, Y.; Suzuki, K.; Nitoda, T.;
Yamamoto, I. Bioorg. Med. Chem. Lett. 2004, 14, 623–
627.
9. Lahmann, M.; Thiem, J. Carbohydr. Res. 1997, 299, 23–
31.
10. Uhrig, R. K.; Picard, M. A.; Beyreuther, K.; Wiessler, M.
Carbohydr. Res. 2000, 325, 72–80.
11. Giorgi, G.; Ponticelli, F.; Salvini, L.; Trendafilova, A.;
Valoti, M.; Pessina, F. Eur. J. Org. Chem. 2003, 106–
115.
12. Kren, V. In Glycoscience: Chemistry and Biology; Fraser-
Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer: Berlin,
2001; Vol. III, pp 2471–2529.
13. Jaramillo, C.; Knapp, S. Synthesis 1994, 1–20.
14. Kalvoda, L. Coll. Czech. Chem. Commun. 1973, 38, 1679–
1692.
15. Ghosez, A.; Go¨bel, T.; Giese, B. Chem. Ber. 1988, 121,
1807–1811.
16. Yamago, S.; Hashidume, M.; Yoshida, J.-i. Tetrahedron
2002, 58, 6805–6813.
17. Robertson, A. J. Chem. Soc. 1929, 1820–1823.
18. Kuribayashi, T.; Ohkawa, N.; Satoh, S. Tetrahedron Lett.
1998, 39, 4537–4540.
Acknowledgments
´
ˆ
Grants from Region Rhone-Alpes (France) and Shang-
hai City Council (PR China) for collaboration (MIRA
program), and from National Science Foundation of
China (NSFC, Grant No. 20176010) are gratefully
acknowledged. Colleagues participating in biological
investigations (N. G. Oikonomakos and co-workers,
Institute of Organic and Pharmaceutical Chemistry,
Athens, 116 35, Greece; J. Li, Chinese National Center
for Drug Screening, Shanghai Institute of Materia
Medica, Shanghai, 200031, PR China) are warmly
´
´
´
thanked. We also thank Lazslo Somsak (Department
of Chemistry, University of Debrecen, Hungary) for
providing us with a sample of 6.
19. Kuribayashi, T.; Mizumo, Y.; Gohya, S.; Satoh, S. J.
Carbohydr. Res. 1999, 18, 371–382.
20. Martin Owton, W. J. Chem. Soc. Perkin Trans. 1 1999,
2409–2420.
Supplementary data
21. Dargelos, A.; Migliaccio, J.; Chaillet, M. Tetrahedron
1971, 27, 5673–5681.
22. Kotha, S.; Kuki, A. Chem. Lett. 1993, 299–302.
23. Bergel, F.; Copping, A. M.; Jacob, A.; Todd, A. R.; Work,
T. S. J. Chem. Soc. 1938, 1382–1384.
Supplementary data associated with this article can be
24. Scott, J. W.; Bizzarro, F. T.; Parrish, D. R.; Saucy, G.
Helv. Chim. Acta 1976, 59, 290–306.
References and notes
25. Mayer, H.; Schudel, P.; Ruegg, R.; Isler, O. Helv. Chim.
¨
Acta 1963, 46, 650–671, and references therein.
26. Oikonomakos, N. G.; Kosmopoulou, M.; Zographos, S.
1. Methods in Enzymology, Oxygen Radicals in Biological
Systems; Packer, L., Ed.; Academic Press, 1994; part C,
Vol. 233; part D, Vol. 234; Oxidants and Antioxidants;
Packer, L., Ed.; Academic Press, 1999; part A, Vol. 299;
part B, Vol. 300.
´
E.; Leonidas, D. D.; Chrysina, E. D.; Somsak, L.; Nagy,
V.; Praly, J.-P.; Docsa, T.; Toth, B.; Gergely, P. Eur. J.
Org. Chem. 2002, 269, 1684–1696.
27. Oikonomakos, N. G.; He, L.; Praly, J.-P., unpublished
results.
28. Chen, R. M.; Hu, L.-H.; An, T. Y.; Li, J.; Shen, Q. Bioorg.
Med. Chem. Lett. 2002, 12, 3387–3390.
29. Li, Y.-F.; Hu, L.-H.; Lou, F.-C.; Li, J.; Shen, Q. J. Asian
Nat. Prod. Res. 2005, 7, 13–18.
30. Tonks, N. K. FEBS Lett. 2003, 546, 140–148.
31. Bialy, L.; Waldmann, H. Angew. Chem., Int. Ed. 2005, 44,
3814–3839.
2. Gordon, M. H. Nat. Prod. Rep. 1996, 13, 265–273.
3. Wright, J. S.; Johnson, E. R.; DiLabio, G. A. J. Am.
Chem. Soc. 2001, 123, 1173–1183.
4. Amorati, R.; Ferroni, F.; Pedulli, G. F.; Valgimigli, L.
J. Org. Chem. 2003, 68, 9654–9658.
5. Afri, M.; Ehrenberg, B.; Talmon, Y.; Schmidt, J.; Cohen,
Y.; Frimer, A. A. Chem. Phys. Lipids 2004, 131, 107–121.
6. Hussain, H. H.; Babic, G.; Durst, T.; Wright, J. S.;
Flueraru, M.; Chichirau, A.; Chepelev, L. L. J. Org.
Chem. 2003, 68, 7023–7032.
32. Fu¨rstner, A. Eur. J. Org. Chem. 2004, 943–958.
33. Shrestha, S.; Shim, Y. S.; Kim, K. C.; Lee, K.-H.; Cho, H.
Bioorg. Med. Chem. Lett. 2004, 14, 1923–1926.
7. Adelwo¨hrer, C.; Rosenau, T.; Kosma, P. Tetrahedron
2003, 59, 8177–8182.