Total synthesis of resolvin E1

Tetrahedron Letters

Volumn 50, Issue 44, 2009, Pages 6079-6082

  Ogawa, Narihito ^a   Kobayashi, Yuichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALDEHYDE; ALLYL COMPOUND; BORANE DERIVATIVE; FATTY ACID DERIVATIVE; KETONE DERIVATIVE; LEUKOTRIENE B4; PHOSPHONIUM DERIVATIVE; RESOLVIN E1; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; EPOXIDATION; HYDROBORATION; SYNTHESIS; WITTIG REACTION;

EID: 70149096440     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.061     Document Type: Article

References (36)

1. Serhan C.N. Prostaglandins Leukotrienes 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. Masoodi M., Mir A.A., Petasis N.A., Serhan C.N., and Nicolaou A. Rapid Commun. Mass Spectrom. 22 (2008) 75-83
7. 4:. Tsuji F., Horiuchi M., Enomoto H., and Aono H. Curr. Top. Pharmacol. 9 (2005) 71-79
8. Toda A., Yokomizo T., and Shimizu T. Prostaglandins Other Lipid Mediat. 68-69 (2002) 575-585
9. Yokomizo T., Izumi T., and Shimizu T. Arch. Biochem. Biophys. 385 (2001) 231-241
10. 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
11. Sato F., and Kobayashi Y. Synlett (1992) 849-857
12. Corey E.J., Marfat A., Goto G., and Brion F. J. Am. Chem. Soc. 102 (1980) 7984-7985
13. Guindon Y., Zamboni R., Lau C.-K., and Rokach J. Tetrahedron Lett. 23 (1982) 739-742
14. Zamboni R., and Rokach J. Tetrahedron Lett. 23 (1982) 2631-2634
15. Corey E.J., Marfat A., Munroe J., Kim K.S., Hopkins P.B., and Brion F. Tetrahedron Lett. 22 (1981) 1077-1080
16. Nicolaou K.C., Zipkin R.E., Dolle R.E., and Harris B.D. J. Am. Chem. Soc. 106 (1984) 3548-3551
17. Kobayashi Y., Shimazaki T., Taguchi H., and Sato F. J. Org. Chem. 55 (1990) 5324-5335
18. Petasis, N. A. U.S. Patent Appl. Publ. (2005), US 2005228047 A1 20051013; Chem. Abstr. 2005, 143, 386846.
19. Nakayama Y., Kumar G.B., and Kobayashi Y. J. Org. Chem. 65 (2000) 707-715
20. Martin V.S., Woodard S.S., Katsuki T., Yamada Y., Ikeda M., and Sharpless K.B. J. Am. Chem. Soc. 103 (1981) 6237-6240
21. 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
22. Kitano Y., Matsumoto T., and Sato F. Tetrahedron 44 (1988) 4073-4086
23. Another possible synthesis of 11 is kinetic resolution of the corresponding racemic γ-cyanoallylic alcohol, which would be proceed slowly:. Yamakawa I., Urabe H., Kobayashi Y., and Sato F. Tetrahedron Lett. 32 (1991) 2045-2048
24. Other syntheses of optically active γ-cyanoallylic alcohols:. Ono T., Tamaoka T., Yuasa Y., Matsuda T., Nokami J., and Wakabayashi S. J. Am. Chem. Soc. 106 (1984) 7890-7893
25. Tanikaga R., Hosoya K., and Kaji A. Chem. Lett. 16 (1987) 829-832
26. Kitano Y., Matsumoto T., Wakasa T., Okamoto S., Shimazaki T., Kobayashi Y., Sato F., Miyaji K., and Arai K. Tetrahedron Lett. 28 (1987) 6351-6354
27. Abe H., Nitta H., Mori A., and Inoue S. Chem. Lett. 21 (1992) 2443-2446
28. Baeza A., Casas J., Nájera C., and Sansano J.M. J. Org. Chem. 71 (2006) 3837-3848
29. Hagiwara H., Isobe K., Numamae A., Hoshi T., and Suzuki T. Synlett (2006) 1601-1603
30. 2O-toluene, 97%.
31. 2 also gave a mixture.
32. Matsumura K., Hashiguchi S., Ikariya T., and Noyori R. J. Am. Chem. Soc. 119 (1997) 8738-8739
33. Zhang H.X., Guibé F., and Balavoine G. J. Org. Chem. 55 (1990) 1857-1867
34. 10
35. 1H NMR spectrum of the free acid (RvE1) is not given in Ref. 10.
36. On the other hand, purity of the methyl ester over the (6E)-isomer was ca. 85%.