Total synthesis of an antioxidant isolated from yeast via palladium- catalyzed coupling and its application for related compounds

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 7, 1999, Pages 1029-1032

  Jinno, Shuji ^a   Okita, Takaaki ^a   Inouye, Kuniyo ^b  

^a NIPPON SUISAN KAISHA LTD   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; BENZODIOXOLE DERIVATIVE; BENZOFURAN DERIVATIVE; CARBON TETRACHLORIDE; PALLADIUM; TOCOPHEROL; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CATALYST; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; GUINEA PIG; LIVER MICROSOME; NONHUMAN;

ANIMALS; ANTIOXIDANTS; CATALYSIS; DIOXOLES; GUINEA PIGS; LIPID PEROXIDATION; MICROSOMES, LIVER; PALLADIUM; SACCHAROMYCES CEREVISIAE;

ANIMALIA; CAVIA PORCELLUS; SUS SCROFA;

EID: 0033526113     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00126-2     Document Type: Article

References (16)

1. 1 Forbes, M.; Zilliken, F.; Roberts, G.; György P. J. Am. Chem. Soc. 1958, 80, 385.
2. 2 Meisinger, M. A. P.; Kuehl, Jr., F. A.; Rickes, E. L.; Brink, N. G.; Folkers, K.; Forbes, M.; Zilliken, F.; Roberts, G.; Gyorgy P. J. Am. Chem. Soc. 1959, 81, 4979.
3. 3 Wagner, A. F.; Walton, E.; Wilson, A. N.; Rodin, J. O.; Holly, F. W.; Brink, N. G.; Folkers, K. J. Am. Chem. Soc. 1959, 81, 4983.
4. 4 Wagner, A. F.; Wilson, A. N.; Folkers, K. J. Am. Chem. Soc. 1959, 81, 5441.
5. 5 McKittrick, B. A.; Stevenson, R. J. Chem. Soc., Perkin Trans. I 1984, 709.
6. 6 O'Keefe D. F.; Dannock M. C; Marcuccio S. M. Tetrahedron Lett. 1992, 33, 6679. For a review, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
7. 6 O'Keefe D. F.; Dannock M. C; Marcuccio S. M. Tetrahedron Lett. 1992, 33, 6679. For a review, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
8. 7 Mann, I. S.; Widdowson, D. A. Tetrahedron 1991, 47, 7991. For a review, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1997; Vol. 50.
9. 7 Mann, I. S.; Widdowson, D. A. Tetrahedron 1991, 47, 7991. For a review, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1997; Vol. 50.
10. 3) 3.95 (s, 3H), 5.01 (s, 2H), 5.95(s, 2H), 6.39 (s, 1H), 6.83 (s, 1H), 6.8-7.6 (m, 9H).
11. 9 Badone, D.; Baroni, M.; Cardamone, A.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170.
12. 3) 3.87 (s, 3H), 4.86 (brs, 1H), 5.91 (s, 2H), 6.33 (s, 1H), 7.35-7.41 (m, 3H,), 7.44-7.48 (m, 2H), 7.63-7.65 (m, 2H), 7.68-7.71 (m, 2H).
13. 3) 3.91 (s, 3H), 4.96 (s, 2H), 5.92 (s, 2H), 6.36 (s, 1H), 6.47-6.48 (m, 1H), 7.27-7.33 (m, 6H), 7.52 (m, 1H).
14. 3) 3.91 (s, 3H), 5.21 (brs, 1H), 5.91 (s, 2H), 6.31 (s, 1H), 7.06 (dd, J = 0.8, 3.5 Hz, 1H), 7.15 (dd, J= 3.5, 5.0 Hz, 1H), 7.48 (dd, J= 0.8, 5.0 Hz, 1H).
15. 13 Assayed in MDS Panlabs. Mansuy, D.; Sassi, A; Dansette, P. M.; Plat, M. Biochem. Biophys. Res. Comm. 1986, 135, 1015.
16. 14 Albano, E.; Lott, K. A. K.; Slater, T. F.; Stier, A.; Symons, M. C. R.; Tomasi, A. Biochem. J. 1982, 204, 593.