2098
C. J. Bennett et al. / Bioorg. Med. Chem. 12 (2004) 2079–2098
24. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org.
Chem. 1996, 61, 5169–5171.
stirred for 22 h to give 64 (0.109 g, 38%) as a brown oil.
This was used without further purification.
25. Ahmad, S.; Doweyko, L. M.; Dugar, S.; Grazier, N.; Ngu,
K.; Wu, S. C.; Yost, K. J.; Chen, B. C.; Gougoutas, J. Z.;
DiMarco, J. D.; Lan, S. J.; Gavin, B. J.; Chen, A. Y.;
Dorso, C. R.; Serafino, R.; Kirby, M.; Atwal, K. S.
J. Med. Chem. 2001, 44, 3302–3310.
Acknowledgements
26. Cockerill, G. S.; Easterfield, H. J.; Percy, J. M.; Pintat, S.
J. Chem. Soc., Perkin Trans. 1 2000, 2591–2599.
27. O’Connor, S. J.; Barr, K. J.; Wang, L.; Sorensen, B. K.;
Tasker, A. S.; Sham, H.; Ng, S. C.; Cohen, J.; Devine, E.;
Cherian, S.; Saeed, B.; Zhang, H. C.; Lee, J. Y.; Warner,
R.; Tahir, S.; Kovar, P.; Ewing, P.; Alder, J.; Mitten, M.;
Leal, J.; Marsh, K.; Bauch, J.; Hoffman, D. J.; Sebti, S.
M.; Rosenberg, S. H. J. Med. Chem. 1999, 42, 3701–3710.
28. Cockerill, G. S.; Easterfield, H. J.; Percy, J. M. Tetrahe-
dron Lett. 1999, 40, 2601–2604.
29. Negishi, E.; Liu, F. In Metal-Catalyzed Cross-Coupling
Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH:
1998; pp 1–47.
30. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.;
Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106,
158–163.
Scottish Enterprise Proof of Concept Fund. Scottish
Executive Environment and Rural Affairs Department
(SEERAD).
References and notes
1. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology
and Medicine, 3rd ed.; Oxford University Press: Oxford,
1999.
2. Duthie, G. G. In Human Nutrition and Dietetics; Garrow,
J. S., James, W. P. T., Ralph, A., Eds.; Churchill
Livingstone: London, 2000; pp 226–236.
3. Bisby, R. H.; Parker, A. W. Arch. Biochem. Biophys. 1995,
317, 170–178.
31. Mahling, J. A.; Jung, K. H.; Schmidt, R. R. Liebigs Ann.
1995, 461–466.
4. Pietta, P.-G. J. Nat. Prod. 2000, 63, 1035–1042.
5. Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.;
Simic, M. G. J. Am. Chem. Soc. 1994, 116, 4846–4851.
6. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Free Rad.
Biol. Med. 1996, 20, 933–956.
7. McPhail, D. B.; Hartley, R. C.; Gardner, P. T.; Duthie, G.
G. J. Agric. Food Chem. 2003, 51, 1684–1690.
8. Mullen, W.; Graf, B. A.; Caldwell, S. T.; Hartley, R. C.;
Duthie, G. G.; Edwards, C. A.; Lean, M. E. J.; Crozier, A.
J. Agric. Food Chem. 2002, 50, 6902–6909.
9. Mitchell, J. H.; Gardner, P. T.; McPhail, D. B.; Morrice,
P. C.; Collins, A. R.; Duthie, G. G. Archiv. Biochem.
Biophys. 1998, 360, 142–148.
10. Vyvyan, J. R.; Holst, C. L.; Johnson, A. J.; Schwenk, C.
M. J. Org. Chem. 2002, 67, 2263–2265.
11. Jinno, S.; Okita, T. Chem. Pharm. Bull. 1998, 46, 1688–
1694.
12. Terashima, K.; Takaya, Y.; Niwa, M. Bioorg. Med. Chem.
2002, 10, 1619–1625.
13. Tziveleka, L.-A.; Kourounakis, A. P.; Kourounakis, P.
N.; Roussis, V.; Vagias, C. Bioorg. Med. Chem. 2002, 10,
935–939.
14. Tamura, K.; Kato, Y.; Ishikawa, A.; Kato, Y.; Himori,
M.; Yoshida, M.; Takashima, Y.; Suzuki, T.; Kawabe, Y.;
Cynushi, O.; Kodama, T.; Niki, E.; Shimizu, M. J. Med.
Chem. 2003, 46, 3083–3093.
€
32. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J.
Tetrahedron 2001, 57, 9225–9283.
33. Spessard, S. J.; Stoltz, B. M. Org. Lett. 2002, 4, 1943–
1946.
34. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am.
Chem. Soc. 1997, 119, 4424–4431.
35. Chhor, R. B.; Nosse, B.; Sorgel, S.; Bohn, C.; Seitz, M.;
Reiser, O. Chem. Eur. J. 2003, 9, 260–270.
36. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc.
1996, 118, 100–110.
37. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413–
4450.
38. Lim, V. S.; Henriquez, C.; Seo, H.; Refetoff, S.; Mertigo,
E. J. J. Clin. Invest. 1980, 66, 946–954.
39. Duthie, G. G.; Gonzalez, B. M.; Morrice, P. C.; Arthur, J.
R. Free Radic. Res. Commun. 1991, 15, 35–40.
40. Badhwar, I. C.; Kang, K. S.; Venkataraman, K. J. Chem.
Soc. 1932, 1107–1112.
41. Beutler, J. A.; Hamel, E.; Vlietinck, A. J.; Haemers, A.;
Rajan, P.; Roitman, J. N.; Cardellina, J. H.; Boyd, M. R.
J. Med. Chem. 1998, 41, 2333–2338.
42. Ross, S. D.; Finkelstein, M.; Petersen, R. C. J. Am. Chem.
Soc. 1964, 86, 4139–4143.
43. Sen, A. B.; Parmar, S. S. J. Indian Chem. Soc. 1954, 31,
709–710.
44. Smith, L. E.; Haller, H. L. J. Am. Chem. Soc. 1939, 61,
143–144.
45. Cushman, M.; Nagarathnam, D.; Gopal, D.; He, H. M.;
Lin, C. M.; Hamel, E. J. Med. Chem. 1992, 35, 2293–2306.
46. Sax, K. J.; Stross, F. S. J. Org. Chem. 1957, 22, 1251–1252.
47. McCarthy, E. D.; Calvin, M. Tetrahedron 1967, 23, 2609–
2619.
48. von Braun, J.; Kroeper, H. Chem. Ber. 1929, 62, 1301–1307.
49. Carreno, M. C.; Ribagorda, M. J. Org. Chem. 2000, 65,
1231–1234.
50. Chang, C. T.; Chen, F. C.; Chen, T. S.; Hsu, K. K.; Ueng,
T.; Hung, M. J. Chem. Soc. 1961, 3414–3417.
51. Garesh, S.; Levy, O.; Markowits, Y.; Shani, A. Tetrahe-
dron 1975, 31, 2803–2807.
52. Brown, H. C.; Basavaiah, D. J. Org. Chem. 1982, 47,
3806–3808.
15. Kubo, I.; Masuoka, N.; Xiao, P.; Haraguchi, H. J. Agric.
Food Chem. 2002, 50, 3533–3539.
16. Kikuzaki, H.; Hisamoto, M.; Hirose, K.; Akiyama, K.;
Taniguchi, H. J. Agric. Food Chem. 2002, 50, 2161–2168.
17. Wagner, H. In The Flavonoids; Harborne, J. B., Mabry, T.
J., Mabry, H., Eds.; Chapman and Hall: London, 1975;
pp 144–146.
18. Chen, F. C.; Chang, C. T. J. Chem. Soc. 1958, 146–150.
19. Molander, G. A.; Yun, C. S. Tetrahedron 2002, 58, 1465–
1470.
20. Miyaura, N.; Ishiyama, T.; Ishikawa, M.; Suzuki, A.
Tetrahedron Lett. 1986, 27, 6369–6372.
21. Zou, G.; Reddy, Y. K.; Falck, J. R. Tetrahedron Lett.
2001, 42, 7213–7215.
22. Molander, G. A.; Ito, T. Org. Lett. 2001, 3, 393–396.
23. Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org.
Chem. 1994, 59, 6095–6097.