New convenient synthesis of iridol. An approach to the synthesis of ubiquinones

Tetrahedron Letters

Volumn 46, Issue 8, 2005, Pages 1255-1257

  Bovicelli, Paolo ^a   Antonioletti, Roberto ^a   Barontini, Maurizio ^a   Borioni, Giorgio ^a   Bernini, Roberta ^b   Mincione, Enrico ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF TUSCIA   (Italy)

Author keywords

Coenzyme Q; Halogenations; Iridol; Ubiquinones

Indexed keywords

2,3 DIMETHOXY 5 METHYLPHENOL; IRIDIUM COMPLEX; PARA CRESOL; UBIQUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 13244277627     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.001     Document Type: Article

References (23)

1. J. Kaikkonen, K. Nyyssonen, E. Porkkala-Sarataho, S.H. Poulsen, T. Metsa-Ketela, M. Hayn, R. Salonen, and J.T. Salosen Free Radical Biol. Med. 22 1997 1195 1202 and references cited therein
2. B.H. Lipshutz, P. Mollard, S.S. Pfeiffer, and W. Chrisman J. Am. Chem. Soc. 124 2002 14282 14283 and references cited therein
3. L. Walter, V. Nogueira, X. Leverve, M.P. Heitz, P. Bernardi, and E. Fontaine J. Biol. Chem. 275 2000 29521 29527
4. M.W. Bader, T. Xie, C.A. Yu, and J.C. Bardwell J. Biol. Chem. 275 2000 26082 26088
5. D. Georgellis, O. Kwon, and E.C. Lin Science 292 2001 2314 2316
6. A. Kalen, B. Norling, E.L. Appelkvist, and G. Dallner Biochim. Biophys. Acta 926 1987 70 78
7. D.Y. He, L.Q. Gu, L. Yu, and C.A. Yu Biochemistry 33 1994 880 884
8. L. Lu, and F. Chen Synth. Commun. 34 22 2004 4049 4053
9. Y. Masaki, K. Hashimoto, and K. Kaji Chem. Pharm. Bull. 32 1994 3952 3958
10. E. Keinan, and D. Eren J. Org. Chem. 52 1987 3872 3875
11. A. Merz, and M. Rauschel Synthesis 1993 797 802
12. Lipshutz, B. H. US 6,545,184 B1 (2003-04-08)
13. L. Blaha, and J. Weichet Collect. Czechoslov. Chem. Commun. 30 1965 2068 2073
14. P. Bovicelli, E. Mincione, R. Antonioletti, R. Bernini, and M. Colombari Synth. Commun. 31 2001 67
15. P. Bovicelli, R. Bernini, R. Antonioletti, and E. Mincione Tetrahedron Lett. 43 2002 5563
16. 2)
17. R.G.R. Bacon, and O.J. Stewart J. Chem. Soc. (C) 1969 301 308
18. R.G.R. Bacon, and S.C. Rennison J. Chem. Soc. (C) 1969 308 312
19. R.G.R. Bacon, and S.C. Rennison J. Chem. Soc. (C) 1969 312 315
20. For mechanistic considerations see: H.L. Aalten, G. van Koten, D.M. Grove, T. Kuilman, O.G. Piekstra, L.A. Hulshof, and R.A. Sheldon Tetrahedron 45 1989 5565 5578
21. For mechanistic considerations of the copper catalysed nucleophilic substitution reaction of sodium methoxide with bromobenzene derivatives see: H.L. Aalten, G. van Koten, D.M. Grove, T. Kuilman, O.G. Piekstra, L.A. Hulshof, and R.A. Sheldon Tetrahedron 45 1989 5565 5578
22. Other bromo aryls such as 2,6-dibromo-4-methyl-phenol, 2-bromo-4-(2-hydroxy-ethyl)-phenol, 2,6-dibromo-4-(2-hydroxy-ethyl)-phenol, 5,5′-dibromo-2,2′-dimethoxy-biphenyl gave the corresponding methoxy derivatives in good to excellent yields
23. I.R. Benzendale, A.-L. Lee, and S.V. Ley Synlett 9 2001 1482