5362
S. Eddarir et al. / Tetrahedron Letters 44 (2003) 5359–5363
19. Fan, X.-S.; Zhang, Y.-M. Chin. J. Chem. 2002, 20, 198–
Acknowledgements
201.
20. Baba, T.; Kizuka, H.; Handa, H.; Ono, Y. Appl. Catal. A
This work was supported by the European Community
(European Contract QLK1-CT-199-00505 POLY-
BIND) and the Conseil Re´gional Nord, Pas-de-Calais,
France. The Mass Spectrometry facility used in this
study was funded by the European Community
(FEDER), the Re´gion Nord-Pas de Calais (France), the
CNRS, and the Universite´ des Sciences et Technologies
de Lille. S.E. thanks the Universite´ Cadi Ayyad, Fac-
ulte´ des Sciences et Technique Gue´liz, Marrakech,
Morocco for a sabbatical leave.
2000, 194-195, 203–211.
21. Eddarir, S.; Abdelhadi, Z.; Rolando, C. Tetrahedron Lett.
2001, 42, 9127–9130.
22. Haddach, M.; McCarthy, J. R. Tetrahedron Lett. 1999,
40, 3109–3112.
23. Cho, C. S.; Itotani, K.; Uemura, S. J. Organomet. Chem.
1993, 443, 253–259.
24. Bumagin, N. A.; Korolev, D. N. Tetrahedron Lett. 1999,
40, 3057–3060.
25. Chen, H.; Deng, M.-Z. Org. Lett. 2000, 2, 1649–1651.
26. Kabalka, G. W.; Malladi, R. R.; Tejedor, D.; Kelley, S.
Tetrahedron Lett. 2000, 41, 999–1001.
27. Goossen, L. J.; Ghosh, K. Angew. Chem., Int. Ed. 2001,
40, 3458–3460.
References
28. Goossen, L. J.; Ghosh, K. J. Chem. Soc., Chem. Com-
mun. 2001, 20, 2084–2085.
29. Kakino, R.; Yasumi, S.; Shimizu, I.; Yamamoto, A. Bull.
Chem. Soc. Jpn. 2002, 75, 137–148.
30. Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122,
11260–11261.
1. Forkmann G.; Heller W. In Comprehensive Natural Prod-
ucts Chemistry; Barton, D.; Nakanishi, K.; Meth-Cohn,
O., Eds. Biosynthesis of flavonoids. Elsevier Science:
Amsterdam, 1999; pp. 713–748.
2. Tomas-Barberan, F. A.; Clifford, M. N. J. Sci. Food
Agric. 2000, 80, 1073–1080.
31. Frost, C. G.; Wadsworth, K. J. J. Chem. Soc., Chem.
Commun. 2001, 2316–2317.
3. Jez, J. M.; Bowman, M. E.; Noel, J. P. Biochemistry
2002, 41, 5168–5176.
4. Bohm, B. A. Introduction to Flavonoids; Harwood Aca-
demic: Amsterdam, 1998.
5. Edwards, M. L.; Stemerick, D. M.; Sunkara, P. S. J.
Med. Chem. 1990, 33, 1948–1954.
6. Bois, F.; Beney, C.; Boumendjel, A.; Mariotte, A. M.;
Conseil, G.; Di Pietro, A. J. Med. Chem. 1998, 41,
4161–4164.
32. Moughamir, K.; Atmani, A.; Mestdagh, H.; Rolando, C.;
Francesch, C. Tetrahedron Lett. 1998, 39, 7305–7306.
33. Portnoy, M.; Milstein, D. Organometallics 1993, 12,
1665–1673.
34. Weissman, H.; Milstein, D. Chem. Commun. 1999, 18,
1901–1902.
35. Murata, M.; Kawakita, K.; Asana, T.; Watanabe, S.;
Masuda, Y. Bull. Chem. Soc. Jpn 2002, 75, 825–829.
36. Takagi, J.; Takahashi, K.; Ishiyama, T.; Miyaura, N. J.
Am. Chem. Soc. 2002, 124, 8001–8006.
7. Liu, M.; Wilairat, P.; Go, M.-L. J. Med. Chem. 2001, 44,
4443–4452.
8. Nielsen, S. F.; Christensen, S. B.; Cruciani, G.;
Kharazmi, A.; Liljefors, T. J. Med. Chem. 1998, 41,
4819–4832.
9. Lin, Y.-M.; Zhou, Y.; Flavin, M. T.; Zhou, L.-M.; Nie,
W.; Chen, F.-C. Bioorg. Med. Chem. 2002, 10, 2795–
2802.
10. Furman, C.; Lebeau, J.; Fruchart, J.-C.; Bernier, J.-L.;
Duriez, P.; Cotelle, N.; Teissier, E. J. Biochem. Mol.
Toxicol. 2001, 15, 270–278.
11. Herencia, F.; Ferrandiz, M. L.; Ubeda, A.; Guillen, I.;
Dominguez, J. N.; Charris, J. E.; Lobo, G. M.; Alcaraz,
M. J. Free Rad. Biol. Med. 2001, 30, 43–50.
12. Rojas, J.; Paya, M.; Dominguez, J. N.; Luisa Ferrandiz,
M. Bioorg. Med. Chem. Lett. 2002, 12, 1951–1954.
13. Yang, E. B.; Guo, Y. J.; Zhang, K.; Chen, Y. Z.; Mack,
P. Biochim. Biophys. Acta 2001, 1550, 144–152.
14. Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J.;
Troth, J. R.; Coffen, D. L. Tetrahedron 1998, 54, 4085–
4096.
15. Daskiewicz, J. B.; Comte, G.; Barron, D.; Di Pietro, A.;
Thomasson, F. Tetrahedron Lett. 1999, 40, 7095–7098.
16. Sebti, S.; Solhy, A.; Tahir, R.; Boulaajaj, S.; Mayoral, J.
A.; Fraile, J. M.; Kossir, A.; Oumimoun, H. Tetrahedron
Lett. 2001, 42, 7953–7955.
37. Henaff, N.; Whiting, A. Tetrahedron 2000, 56, 5193–
5204.
38. Schummer, D.; Hoefle, G. Tetrahedron 1995, 51, 11219–
11222.
39. Falck, J. R.; Bondlela, M.; Venkataraman, S. K.; Srini-
vas, D. J. Org. Chem. 2001, 66, 7148–7150.
40. Breit, B.; Winde, R.; Mackewitz, T.; Paciello, R.; Harms,
K. Chem. Eur. J. 2001, 7, 3106–3121.
41. Parmar, V. S.; Jain, S. C.; Bisht, K. S.; Sharma, N. K.;
Himanshu; Gupta, S.; Prasad, A. K.; Jha, A.; Poonam;
Malhotra, S.; Sharma, S. K.; Bracke, M. E.; Errington,
W.; Olsen, C. E.; Wengel, J. Indian J. Chem., Sect B
1998, 37B, 628–643.
42. Nay, B.; Collet, M.; Lebon, M.; Cheze, C.; Vercauteren,
J. Tetrahedron Lett. 2002, 43, 2675–2678.
43. Nay, B.; Peyrat, J.-F.; Vercauteren, J. Eur. J. Org. Chem.
1999, 9, 2231–2234.
44. Typical procedure for the preparation of chalcones from
benzoyl chlorides and phenylvinylboronic acids: E-2-
phenylethenyl-boronic acid (74 mg, 0.5 mmol), benzoyl
chloride (2 equiv., 141 mg,
1
mmol), Tetra-
kis(triphenylphosphine)palladium(0) (17 mg, 3%), cesium
carbonate (5 equiv., 814 mg, 2.5 mmol) and 5 mL of
freshly distilled toluene were added in a flask fitted with
a reflux condenser. After flushing with argon the flask
was heated at reflux 4 h. After cooling, the organic phase
was diluted with ethyl acetate then washed with saturated
sodium hydrogenocarbonate then with water and dried
17. Bennett, M.; Burke, A. J.; O’Sullivan, W. I. Tetrahedron
1996, 52, 7163–7178 and 1998, 54, 9911.
18. Bose, G.; Mondal, E.; Khan, A. T.; Bordoloi, M. J.
Tetrahedron Lett. 2001, 42, 8907–8909.