Total synthesis of resolvin E2

Tetrahedron Letters

Volumn 51, Issue 14, 2010, Pages 1856-1859

  Kosaki, Yusuke ^a   Ogawa, Narihito ^a   Kobayashi, Yuichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; RESOLVIN E2; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; OXIDATION; OZONOLYSIS; STEREOCHEMISTRY; WITTIG REACTION;

EID: 77549087702     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.01.109     Document Type: Article

References (36)

1. Serhan C.N. Prostaglandins Leukot. Essent. Fatty Acids 79 (2008) 157-163
2. Serhan C.N., Chiang N., and Van Dyke T.E. Nat. Rev. Immun. 8 (2008) 349-361
3. Serhan C.N., Gotlinger K., Hong S., and Arita M. Prostaglandins Other Lipid Mediat. 73 (2004) 155-172
4. Schwab J.M., Chiang N., Arita M., and Serhan C.N. Nature 447 (2007) 869-874
5. Arita M., Bianchini F., Aliberti J., Sher A., Chiang N., Hong S., Yang R., Petasis N.A., and Serhan C.N. J. Exp. Med. 201 (2005) 713-722
6. Ogawa N., and Kobayashi Y. Tetrahedron Lett. 50 (2009) 6079-6082
7. Ogawa S., Urabe D., Yokokura Y., Arai H., Arita M., and Inoue M. Org. Lett. 11 (2009) 3602-3605
8. 5,12-diHETE:. Borgeat P., Fruteau de Laclos B., Picard S., Drapeau J., Vallerand P., and Corey E.J. Prostaglandins 23 (1982) 713-724
9. Lee T.H., Menica-Huerta J.-M., Shih C., Corey E.J., Lewis R.A., and Austen K.F. J. Biol. Chem. 259 (1984) 2383-2389
10. 5,15-diHETE:. Maas R.L., Turk J., Oates J.A., and Brash A.R. J. Biol. Chem. 257 (1982) 7056-7067
11. Chavis C., Chanez P., Vachier I., Bousquet J., Michel F.B., and Godard P. Biochem. Biophys. Res. Commun. 207 (1995) 273-279
12. Chavis C., Vachier I., Chanez P., Bousquet J., and Godard P. J. Exp. Med. 183 (1996) 1633-1643
13. Rokach J., Guindon Y., Young R.N., Adams J., and Atkinson J.G. In: ApSimon J. (Ed). The Total Synthesis of Natural Products Vol. 7 (1988), Wiley, New York 141
14. Sato F., and Kobayashi Y. Synlett (1992) 849-857
15. 5,12-diHETE:. Corey E.J., Mrfat A., and Laguzza B.C. Tetrahedron Lett. 22 (1981) 3339-3342
16. Adams J., Leblanc Y., and Rokach J. Tetrahedron Lett. 25 (1984) 1227-1230
17. 5,15-diHETE:. Nicolaou K.C., and Webber S.E. J. Am. Chem. Soc. 106 (1984) 5734-5736
18. Kitano Y., Matsumoto T., and Sato F. Tetrahedron 44 (1988) 4073-4086
19. Martin V.S., Woodard S.S., Katsuki T., Yamada Y., Ikeda M., and Sharpless K.B. J. Am. Chem. Soc. 103 (1981) 6237-6240
20. Gao Y., Klunder J.M., Hanson R.M., Ko S.Y., Masamune H., and Sharpless K.B. J. Am. Chem. Soc. 109 (1987) 5765-5780
21. Similar compounds which possess the alkoxy or acyloxy group instead of the TBSO group have been synthesized:. Guidon Y., Zamboni R., Lau C.-K., and Rokach J. Tetrahedron Lett. 23 (1982) 739-742
22. Spur B., Crea A., and Peters W. Arch. Pharm. 318 (1985) 225-228
23. Pianetti P., Rollin P., and Pougny J.R. Tetrahedron Lett. 27 (1986) 5853-5856
24. Leblanc Y., Fitzsimmons B., Adams J., and Rokach J. Tetrahedron Lett. 26 (1985) 1399-1402
25. Gravier-Pelletier C., Dumas J., Merrer Y.L., and Depezay J.-C. Tetrahedron 48 (1992) 2441-2452
26. Peng Z.-H., Li Y.-L., Wu W.-L., Liu C.-X., and Wu Y.-L. J. Chem. Soc., Perkin Trans. 1 (1996) 1057-1066
27. Sellès P., and Lett R. Tetrahedron Lett. 43 (2002) 4621-4625
28. Nakayama Y., Kumar G.B., and Kobayashi Y. J. Org. Chem. 65 (2000) 707-715
29. Kobayashi Y., Shimazaki T., Taguchi H., and Sato F. J. Org. Chem. 55 (1990) 5324-5335
30. Büchi G., and Wüest H. J. Am. Chem. Soc. 100 (1978) 294-295
31. Avery M.A., Chong W.K.M., and Jennings-White C. J. Am. Chem. Soc. 114 (1992) 974-979
32. Avery M.A., Jennings-White C., and Chong W.K.M. J. Org. Chem. 54 (1989) 1789-1792
33. Murakami M., Sakita K., Igawa K., and Tomooka K. Org. Lett. 8 (2006) 4023-4026
34. Igawa K., Sakita K., Murakami M., and Tomooka K. Synthesis (2008) 1641-1645
35. 1H NMR spectroscopy of the corresponding MTPA ester, thus confirming no racemization. The transformation was applied to that delineated in Scheme 6.{A figure is presented}
36. 3) δ -4.7 (+), -4.2 (+), 9.1 (+), 18.3 (-), 19.5 (-), 20.8 (-), 25.9 (+), 26.0 (-), 26.1 (-), 27.1 (+), 30.7 (-), 34.1 (-), 37.7 (-), 51.5 (+), 72.8 (+), 75.3 (+), 124.5 (+), 125.2 (+), 127.4 (+), 127.5 (+), 128.1 (+), 128.31 (+), 128.33 (+), 128.5 (+), 129.1 (+), 129.4 (+), 129.5 (+), 129.6 (+), 134.4 (-), 134.6 (-), 136.0 (-), 136.1 (-), 136.2 (-), 137.0 (-), 174.1 (-).