Synthesis of methyl (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11, 13-hexadecatetraenoate, an analogue of 15R-lipoxin A4

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 19, 2003, Pages 3223-3226

  Phillips, Eifion D ^a   Chang, Hui Fang ^a   Holmquist, Christopher R ^a   McCauley, John P ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXY 2 RIBOSE; ACETIC ACID DERIVATIVE; ALDEHYDE; CARBON; CHEMICAL COMPOUND; DECANE; LIPOXIN A; METHYL 16 (4 FLUOROPHENOXY) 5,6,15 TRIHYDROXY 7,9,11,13 HEXADECATETRAENOATE; METHYL(TRIPHENYLPHOSPHORANYLIDINE)ACETATE; PALLADIUM; RIBOSE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; HYDROGENATION; OXIDATION; PROTEIN SYNTHESIS; REDUCTION; WITTIG REACTION;

EID: 0042833002     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00667-X     Document Type: Article

References (29)

1. Serhan C.N., Chiang N. Sci. World J. 2:2002;169.
2. Samuelsson B., Dahlén S.-E., Lindgren J. Å., Rouzer C.A., Lynch S. Science. 237:1987;1171.
3. Godson C., Brady H.R. Curr. Opin. Invest. Drugs. 1:2000;380.
4. McMahon B., Mitchell S., Brady H.R., Godson C. Trends Pharmacol. Sci. 22:2001;391.
5. Serhan C.N. Prostaglandins Other Lipid Mediators. 68-69:2002;433.
6. Serhan C.N. Curr. Med. Chem. Anti-Inflamm. Anti-Allergy Agents. 1:2002;177.
7. Serhan C.N., Fiore S., Brezinski D.A., Lynch S. Biochemistry. 32:1993;6313.
8. Maddox J.F., Serhan C.N. J. Exp. Med. 183:1996;137.
9. Serhan C.N., Maddox J.F., Petasis N.A., Akritopoulou-Zanze I., Papayianni A., Brady H.R., Colgan S.P., Madara J.L. Biochemistry. 34:1995;14609.
10. Clish C.B., O'Brien J.A., Gronert K., Stahl G.L., Petasis N.A., Serhan C.N. Proc. Natl. Acad. Sci. U.S.A. 96:1999;8247.
11. Fierro I.M., Kutock J.L., Serhan C.N. J. Pharm. Exp. Ther. 300:2002;385.
12. Gervitz A.T., Collier-Hyams L.S., Young A.N., Kucharzik T., Guilford W.J., Parkinson J.F., Williams I.R., Neish A.S., Madara J.L. J. Immunol. 168:2002;5260.
13. Leonard M.O., Hannan K., Burne M.J., Lappin D.W.P., Doran P., Coleman P., Stenson C., Taylor C.T., Daniels F., Godson C., Petasis N.A., Rabb H., Brady H.R. J. Am. Soc. Nephrol. 13:2002;1657.
14. Nicolaou K.C., Veale C.A., Webber S.E., Katerinopoulos H. J. Am. Chem. Soc. 107:1985;7515.
15. Nicolaou K.C., Marron B.E., Veale C.A., Webber S.E., Serhan C.N. J. Org. Chem. 54:1989;5527.
16. Yadav J.S., Barma D.K., Dutta D. Tetrahedron Lett. 39:1998;143.
17. Akritopoulou-Zanze, I. PhD Dissertation, U. Southern California, 1994.
18. Rodriguez A.R., Spur B.W. Tetrahedron Lett. 42:2001;6057.
19. Lee T.H., Lympany P., Crea A.E.G., Spur B.W. Biochem. Biophys. Res. Commun. 180:1991;1416.
20. Omura K., Swern D. Tetrahedron. 34:1978;1651.
21. (a) Wadsworth, W. S.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733.
22. (b) Wadsworth, W.S. Org. React. 1977, 25, 73.
23. (a) Michaelis, A.; Kaehne, R. Ber. Dtsch. Chem. Ges. 1898, 31, 1048.
24. (b) Arbusov, B. A. Pure Appl. Chem. 1964, 9, 307.
25. Smith R.L., Bicking J.B., Gould N.P., Lee T.-J., Robb C.M., Kuehl F.A., Mandel L.R., Cragoe E.J. J. Med. Chem. 20:1974;540.
26. Corey E.J., Wollenberg R.H. J. Org. Chem. 40:1975;3788.
27. Katsuki T., Sharpless K.B. J. Am. Chem. Soc. 102:1980;5974.
28. Kitano Y., Matsumoto T., Okamoto S., Shimazaki T., Kobayashi Y., Sato F. Chem. Lett. 1987;1523.
29. Boland W., Schroer N., Sieler C., Feigel M. Helv. Chim. Acta. 70:1987;1025.