First total synthesis of 7(S),16(R),17(S)-Resolvin D2, a potent anti-inflammatory lipid mediator

Tetrahedron Letters

Volumn 45, Issue 47, 2004, Pages 8717-8720

  Rodríguez, Ana R ^a   Spur, Bernd W ^a  

^a UMDNJ School of Osteopathic Medicine   (United States)

Author keywords

Hydrolytic kinetic resolution; Palladium catalyst; Reduction; Resolvins; Takai reaction

Indexed keywords

ANTIINFLAMMATORY AGENT; EPOXIDE; LIPID; RESOLVIN D2; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; HYDROLYSIS; HYDROLYSIS KINETICS;

EID: 7244242688     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.129     Document Type: Article

References (25)

1. C.N. Serhan, S. Hong, K. Gronert, S.P. Colgan, P.R. Devchand, G. Mirick, and R.L. Moussignac J. Exp. Med. 196 8 2002 1025 1037
2. S. Hong, K. Gronert, P.R. Devchand, R.L. Moussignac, and C.N. Serhan J. Biol. Chem. 278 17 2003 14677 14687
3. V.L. Marcheselli, S. Hong, W.J. Lukiw, X.H. Tian, K. Gronert, A. Musto, M. Hardy, J.M. Gimenez, N. Chiang, C.N. Serhan, and N.G. Bazan J. Biol. Chem. 278 44 2003 43807 43817 Erratum in: J. Biol. Chem. 278 51 2003 51974
4. P.K. Mukherjee, V.L. Marcheselli, C.N. Serhan, and N.G. Bazan Proc. Natl. Acad. Sci. U.S.A. 101 22 2004 8491 8496
5. C.N. Serhan, and N. Chiang Rheum. Dis. Clin. N. Am. 30 1 2004 69 95
6. C.N. Serhan, K. Gotlinger, S. Hong, and M. Arita Prostag. Oth. Lipid Mediators 73 3-4 2004 155 172
7. L.A. Horrocks, and A.A. Farooqui Prostag. Leukotr. Ess. 70 2004 361 372
8. D. Takai, T. Nagase, and T. Shimizu Nat. Immunol. 5 2004 357 358
9. D.W. Gilroy, T. Lawrence, M. Perretti, and A.G. Rossi Nat. Rev. Drug Discovery 3 2004 401 416
10. E.J. Corey, and W.-g. Su Tetrahedron Lett. 25 1984 5119 5122
11. A. Rodriguez, M. Nomen, B.W. Spur, and J.J. Godfroid Tetrahedron Lett. 39 1998 8563 8566
12. The enantiomeric excess was determined by Chiral-HPLC [column: Chiracel OF, mobile phase: hexane/i-PrOH (75:25) λ = 265 nm]
13. S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunaga, K.B. Hansen, A.E. Gould, M.E. Furrow, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 1307 1315
14. A. Rodriguez, M. Nomen, B.W. Spur, J.-J. Godfroid, and T.H. Lee Tetrahedron 57 2001 25 37
15. A. Rodriguez, M. Nomen, B.W. Spur, and J.J. Godfroid Tetrahedron Lett. 40 1999 5161 5164
16. K. Takai, K. Nitta, and K. Utimoto J. Am. Chem. Soc. 108 1986 7408 7410
17. A.R. Rodriguez, and B.W. Spur Tetrahedron Lett. 44 2003 7411 7415
18. E.J. Corey, A. Marfat, J. Munroe, K.S. Kim, P.B. Hopkins, and F. Brion Tetrahedron Lett. 22 1981 1077 1080
19. J. Morris, and D.G. Wishka Tetrahedron Lett. 27 1986 803 806
20. E.J. Corey, and J.W. Suggs Tetrahedron Lett. 16 1975 2647 2650
21. K.C. Nicolaou, C.A. Veale, S.E. Webber, and H. Katerinopoulos J. Am. Chem. Soc. 107 1985 7515 7518
22. K.C. Nicolaou, and S.E. Webber Synthesis 1986 453 461
23. A.R. Rodriguez, and B.W. Spur Tetrahedron Lett. 42 2001 6057 6060
24. W. Boland, N. Schroer, C. Sieler, and M. Feigel Helv. Chim. Acta 70 1987 1025 1040
25. +