Regioselective halogenation of biphenyls for preparation of valuable polyhydroxylated biphenyls and diquinones

Tetrahedron

Volumn 62, Issue 4, 2006, Pages 635-639

  Bovicelli, Paolo ^a   Antonioletti, Roberto ^a   Onori, Antonella ^a   Delogu, Giovanna ^b   Fabbri, Davide ^b   Dettori, Maria Antonietta ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b CNR   (Italy)

Author keywords

Biphenoquinones; Dimethyldioxirane; Halogenation; Hydroxylated biphenyls

Indexed keywords

BIPHENYL; ETHER DERIVATIVE; NATURAL PRODUCT; QUINONE DERIVATIVE;

ARTICLE; ELECTRON; HALOGENATION; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL;

EID: 28944449326     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.10.009     Document Type: Article

References (55)

1. H. Haraguchi, T. Saito, and H. Ishikawa Planta Med. 62 1996 217 221
2. R.S. Ward Nat. Prod. Rep. 13 1996 43 74
3. V. Cody, E. Middleton, and J.B. Harborne Plant Flavonoids in Biology and Medicine II: Biochemical, Cellular and Medicinal Properties 1998 Liss New York
4. G. Matthée, A.D. Wright, and G.M. König Planta Med. 65 1999 493 506
5. G. Bringmann, M. Breuning, and S. Tasler Synthesis 1999 525 558
6. M. Tene, H.K. Wabo, and P. Kamnaing Phytochemistry 54 2000 975 978
7. M.J. Amiot, and A. Fleuriet J. Agric. Food Chem. 34 1986 823
8. M. Gesell, E. Hammer, and M. Specht Appl. Environ. Microbiol. 2001 1551 4201
9. S. Quideau, and K.S. Feldman J. Org. Chem. 62 1997 8809 8813
10. K.C. Nicolau, N.C. Boddy, S. Brase, and N. Winssinger Angew. Chem., Int. Ed. 38 1999 2096 2152
11. F.F. Paintner, K. Gorler, and W. Voelter Synlett 2003 522 526
12. Y. Amakura, Y. Umino, S. Tsuji, and Y. Tonogai J. Agric. Food Chem. 48 2000 6292 6297
13. J.L. Maas, G.J. Galletta, and G.D. Stoner HortScience 26 1991 10 14
14. Y. Amakura, Y. Umino, S. Tsuji, H. Ito, T. Hatano, T. Yoshida, and Y. Tonogai Food Chem. 77 2002 47 56
15. K. Indira Priyadarsini, S.M. Khopde, S.S. Santosh Kumar, and H. Mohan J. Agric. Food Chem. 50 2002 2200 2206
16. K.-T. Chung, T.Y. Wong, C.-I. Wei, Y.-W. Huang, and Y. Lin Crit. Rev. Food Sci. Nutr. 38 1998 421 464
17. K. Miura, T. Inagaki, and N. Nakatani Chem. Pharm. Bull. 37 1989 1816 1819
18. Y.-C. Shen, Y.-J. Sung, and C.-F. Chen Eur. J. Pharmacol. 343 1998 79 86
19. I. Kruk, T. Michalska, K. Lichszteld, A. Kladna, and H.Y. Aboul-Enein Chemosphere 41 2000 1059 1064
20. J.W. Benbow, B.L. Martinez, and W.R. Anderson J. Org. Chem. 62 1997 9345 9347
21. Y. Fukuyama, and Y. Asakawa J. Chem. Soc. Perkin Trans. 1 1991 2737 2741
22. G. Bringmann, R. Goetz, P.A. Keller, R. Walter, M.R. Boyd, F. Lang, A. Garcia, J.J. Walsh, I. Tellitu, K.V. Bhaskar, and T.R. Kelly J. Org. Chem. 63 1998 1090 1097
23. W.J. van Rensburg, D. Ferreira, E. Malan, and J.A. Steenkamp Phytochemistry 53 2000 285 292
24. S.-p. Hong, and M.C. McIntosh Org. Lett. 4 2002 19 21
25. S. Paraskevas, D. Konstantinidis, and G. Vassilara Synthesis 1988 897 899
26. D. Villemin, and F. Sauvaget Synlett 1994 435 436
27. G.A. Abakumov, V.I. Nevodchikov, N.O. Druzhkov, L.G. Abakumova, Y.A. Kurskii, and V.K. Cherkasov Russ. Chem. Bull. 46 1997 771 776
28. D. Magdziak, A.A. Rodriguez, R.W. Van De Water, and T.R.R. Pettus Org. Lett. 4 2002 285 288
29. M.P. Green, S. Pichlmair, M.M.B. Marques, H.J. Martin, O. Diwald, T. Berger, and J. Mulzer Org. Lett. 6 2004 3131 3134
30. M.B. Andrus, E.L. Meridith, E.J. Hicken, B.L. Simmons, R.R. Glancey, and W. Ma J. Org. Chem. 68 2003 8162 8169
31. T. Takeya, T. Otsuka, I. Okamoto, and E. Kotani Tetrahedron 60 2004 10681 10693
32. P. Bovicelli, E. Mincione, R. Antonioletti, R. Bernini, and M. Colombari Synth. Commun. 31 2001 67
33. P. Bovicelli, R. Bernini, R. Antonioletti, and E. Mincione Tetrahedron Lett. 43 2002 5563
34. G. Delogu, D. Fabbri, M.A. Dettori, A. Forni, and G. Casalone Tetrahedron: Asymmetry 11 2000 4417 4427
35. J.E. Simpson, G.H. Daub, and F.N. Hayes J. Org. Chem. 38 1973 1771 Better yield was obtained using dry acetone instead of DMF
36. P. Bovicelli, R. Antonioletti, M. Barontini, G. Borioni, R. Bernini, and E. Mincione Tetrahedron Lett. 46 2005 1255 1257
37. F.G. Mann, and M.J. Pragnel J. Chem. Soc., Chem. Commun. 1965 4120
38. C.D. Snyder, and H. Rapoport J. Org. Chem. 41 1970 227 231
39. J. Peyton, P.S. Callery, and N. Castagnoni J. Org. Chem. 41 1972 3627 3629
40. B. Errazzuriz, R. Tapia, and J.A. Valderrama Tetrahedron Lett. 26 1985 819 822
41. J.W. Wildess, N.H. Martin, and C.G. Pete J. Org. Chem. 36 1971 721
42. H. Tohma, H. Morioka, S. Takizawa, M. Arisawa, and Y. Kita Tetrahedron 57 2001 345 352
43. J.P. Parrish, V.L. Flanders, R.J. Floyd, and K.W. Jung Tetrahedron Lett. 42 2001 7729 7732
44. J.L. Schulte, S. Laschat, V. Vill, E. Nishikawa, H. Finkelmann, and M. Nimtz Eur. J. Org. Chem. 11 1998 2499 2506
45. D.H. Young, C.M. Tice, E.L. Michelotti, R.C. Roemmele, R.A. Slawecki, F.M. Rubio, and J.A. Rolling Biorg. Med. Chem. Lett. 11 2001 1393 1396
46. J.M. Andreu, B. Perez-Ramirez, M. Gorbunoff, G.D. Ayala, and S.N. Timasheff Biochemistry 37 1998 8356 8368
47. Z. Getahun, L. Jurd, P.S. Chu, C.M. Lin, and E. Hamel J. Med. Chem. 35 1992 1058 1067
48. M.N. Yousaf, B.T. Houseman, and M. Mrksich Angew. Chem., Int. Ed. 40 2001 1093 1096
49. D. Shabat, R.J. Amir, A. Gopin, N. Pessah, and M. Shamis Chem. Eur. J. 10 2004 2626 2634
50. M.R. Agharahimi, and N.A. LeBel J. Org. Chem. 60 1995 1856 1863
51. H. Tohma, H. Morioka, S. Takizawa, M. Arisawa, and Y. Kita Tetrahedron 57 2001 345 352
52. V. Courtois, R. Barhdadi, M. Troupel, and J. Périchon Tetrahedron 53 1997 11569 11576
53. T. Yamato, C. Hideshima, K. Suehiro, M. Tashiro, G.K. Surya Pakash, and G.A. Olah J. Org. Chem. 56 1991 6248 6250
54. Z. Bouaziz, A. Ghérardi, F. Régnier, M.-E. Sarciron, X. Bertheau, B. Fenet, N. Walchshofer, and H. Fillion Eur. J. Org. Chem. 2002 1834 1838
55. S.M. Paraskevas, D. Konstantinidis, and G. Vassilara Synthesis 1988 897 899