New efficient synthesis of ubiquinones

Synthetic Communications

Volumn 38, Issue 3, 2008, Pages 391-400

  Bovicelli, Paolo ^a   Borioni, Giorgio ^a   Fabbrini, Danilo ^a   Barontini, Maurizio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Coenzyme Q; Halogenations; Iridol; Ubiquinones

Indexed keywords

2,3,4 TRIMETHOXY 6 METHYLBENZALDEHYDE; 2,3,4 TRIMETHOXY 6 METHYLPHENOL; 2,3,4 TRIMETHOXY 6 METHYLPHENYL 5 PRENYLPHENOL; 2,3,4 TRIMETHOXY 6 METHYLPHENYL 5 SOLANESYLPHENOL; 2,3,4 TRIMETHOXY 6 METHYLPHENYL PRENYL ETHER; 2,3,4 TRIMETHOXY 6 METHYLPHENYL SOLANESYL ETHER; 5 FARNESYL 2,3,4 TRIMETHOXY 6 METHYLPHENOL; 5 GERANYL 2,3,4 TRIMETHOXY 6 METHYLPHENOL; BENZALDEHYDE; FARNESYL 2,3,4 TRIMETHOXY 6 METHYLPHENYL ETHER; UBIQUINONE; UBIQUINONE DERIVATIVE; UBIQUINONE Q1; UBIQUINONE Q2; UBIQUINONE Q3; UBIQUINONE Q9; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 38649117308     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701771066     Document Type: Article

References (17)

1. Cross, C. E.; Halliwell, E.; Borish, E. T.; Pryor, W. A.; Ames, B. N.; Saul, R. L.; McCord, J. M.; Harman, D. Oxygen radicals and human disease. Ann. Intern. Med. 1987, 107, 526-545.
2. Kagan, V. E.; Serbinova, E. A.; Stoyanovsky, D. A.; Khwaja, S.; Packe. Assay of ubiquinones and ublquinols as antioxidants. Methods Enzymol. 1994 234, 343-354.
3. Lipshutz, B. H.; Mollard, P.; Pfeiffer, S. S.; Chrisman, W. A short, higly efficient synthesis of coenzyme. J. Am. Chem. Soc. 2002, 124, 14282-14283, and references therein.
4. Georgellis, D.; Kwon, O.; Lin, E. C. Quinones as the recloy signal for the Arc two-components system of backteria. Science 2001, 292, 2314-2316.
5. Landi, L.; Cabrini, L.; Fiorentini, D.; Sartor, G.; Pasquali, P.; Masotti, L. The role of the side chain in the antioxidan activity of ubiquinones. Free Radic. Res. Commun. 1991, 14 (1), 1-8.
6. See, for example, Prasad, K. N.; Cole, W. C.; Haase, G. M. Formulations comprising multiple dietary and endogenously made antioxidants and Vitamin B. U.S. Pat. Appl. Publ. 2006263446, 2006.
7. (a) Kishi, T. Fragrance Journal 2005, 33 (8), 21-27;
8. (b) Takahashi, T.; Okamoto, M.; Kishi, T. Biochemical functions of endogenous and exogenous coenzyme. New Food Industry 2003, 45 (7), 1-10.
9. Alleva, R.; Tomasetti, M.; Battino, M.; Curatola, G.; Littarru, G. P.; Folkers, K. The roles of coenzyme Q10 and vitamin E on the peroxidation of human low density lipoprotein subfractions. Proc. Natl. Acad. Sci. USA 1995, 92 (20), 9388-9391.
10. Bovicelli, P.; Mincione, E.; Antonioletti, R.; Bernini, R. Colombari, M. Selective halogenation of aromatics by dimeth. Synth. Commun. 2001, 31, 67.
11. Bovicelli, P.; Antonioletti, R.; Barontini, M.; Borioni, G.; Bernini, R.; Mincione, E. New convenient synthesis of iridol. An approach to synthesis of ubiquinones. Tetrahedron Lett. 2005, 46 (8), 1255-1257.
12. Matsumoto, H.; Kobayashi, H.; Hotta, Y. Acid-catalyzed oxidation of benzaldehydes to phenols by hydorogen peroxide. J. Org. Chem. 1989, 49, 4740-4741.
13. Carruthers, W.; Johnstone, R. A. W. Alcohols of tobacco. Solanesol and n-docosanol. Chem. Ind. 1960, 867-868.
14. Liang, L.; Fener, C. A novel and convenient synthesis of coenzyme Q1. Synth. Commun. 2004, 34 (22), 4049-4053.
15. Adam, W.; Shimizu, M. The acid-catalyzed oxidation of methoxybenzenes to p-benzoquinones by dimethyldioxirane. Synthesis 1994, 6, 560-562.
16. Lipshutz, B. H.; Bulow, G.; Fernandez-Lazaro, F.; Kim, S.-K.; Lowe, R.; Mollard, P.; Stevens, K. L. A convergent approach to coenzyme. J. Am. Chem. Soc. 1999, 121, 11664-11673.
17. Kuznetsova, T. A.; Dmitrenok, A. S.; Sobolevskaya, M. P.; Shevchenko, L. S.; Mikhailov, V. V. Ubiquinone Q9 from a marine isolate of an actinobacterium no cardia sp. Russ. Chem. Bl., Inter. Ed. 2002, 51 (10), 1951-1953.