Concise syntheses of three ω-3 polyunsaturated fatty acids

Tetrahedron Letters

Volumn 53, Issue 44, 2012, Pages 5837-5839

  Jakobsen, Martin Gjerde ^a   Vik, Anders ^a   Hansen, Trond Vidar ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

Docosapentaenoic acid; Eicosatetraenoic acid; Polyunsaturated fatty acids; Stereadonic acid; Stereoselective synthesis

Indexed keywords

DOCOSAPENTAENOIC ACID; ICOSATETRAENOIC ACID; STEARIDONIC ACID;

ARTICLE; DRUG SYNTHESIS; FATTY ACID SYNTHESIS;

EID: 84866774641     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.009     Document Type: Article

References (27)

1. S.C. Larsson, M. Kumlin, M. Ingelman-Sundberg, and A. Wolk Am. J. Clin. Nutr. 79 2004 935
2. J.A. Nettleton, and R. Katz J. Am. Diet. Assoc. 105 2005 428
3. C.R. Harper, and T.A. Jacobson Arch. Intern. Med. 161 2001 2185
4. J.L. Breslow Am. J. Clin. Nutr. 83 2006 1477S
5. L.G. Cleland, M.J. James, and S.M. Proudman Drugs 63 2003 845
6. C.N. Serhan, S. Hong, K. Gronert, S.P. Colgan, P.R. Devchand, G. Mirick, and R.-L. Moussignac J. Exp. Med. 196 2002 1025
7. S. Hong, K. Gronert, P.R. Devchand, R.-L. Moussignac, and C.N. Serhan J. Biol. Chem. 278 2003 14677
8. 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 2003 43807
9. C.N. Serhan, K. Gotlinger, S. Hong, Y. Lu, J. Siegelman, T. Baer, R. Yang, S.P. Colgan, and N.A. Petasis J. Immunol. 2006 1848 176
10. C.N. Serhan, R. Yang, K. Martinod, K. Kasuga, P.S. Pillai, T.F. Porter, S.F. Oh, and M. Spite J. Exp. Med. 206 2009 15
11. C.N. Serhan, and N.A. Petasis Chem. Rev. 111 2011 5922
12. G. Kaur, D. Cameron-Smith, M. Garg, and A.J. Sinclair Prog. Lipid Res. 50 2011 28
13. J.L. Guil-Guerrero Eur. J. Lipid Sci. Technol. 109 2007 1226
14. 3B Scientific (www.3bsc.com): $750 for 5 mg of eicosatetraenoic acid (3); Cayman (http://www.caymanchem.com): $1250 for 10 mg of docosapentaenoic acid (4) and $1000 for 10 mg of stearidonic acid (5), respectively.
15. S. Flock, and L. Skattebol J. Chem. Soc., Perkin Trans. 1 2000 3071
16. A.K. Holmeide, L. Skattebol, and M. Sydnes J. Chem. Soc., Perkin Trans. 1 2001 1942
17. A. Vik, T.V. Hansen, A.K. Holmeide, and L. Skattebol Tetrahedron Lett. 51 2010 2852
18. M.A. Yasser, and T.V. Hansen Pure Appl. Chem. 83 2011 489
19. H.F. Anwar, and T.V. Hansen Org. Lett. 11 2009 587
20. A. Vik, and T.V. Hansen Tetrahedron Lett. 52 2011 1060
21. M. Hamberg, I.R. Chechetkin, A.N. Grechkin, I. Ponce de Leon, C. Castresana, and G. Bannenberg Lipids 41 2006 499
22. A.M. Langseter, L. Skattebol, and Y. Stenstrom Tetrahedron Lett. 53 2012 940
23. R. Tyagi, B. Shimpukade, S. Blaettermann, E. Kostenis, and T. Ulven Med. Chem. Commun. 3 2012 195
24. S. Flock, M. Lundquist, and L. Skattebol Acta Chem. Scand. 53 1999 436
25. A.K. Holmeide, and L. Skattebol J. Chem. Soc., Perkin Trans. 1 2000 2271
26. B.S. Bal, W.E. Childers Jr., and H.W. Pinnick Tetrahedron 37 1981 2091
27. D.V. Kuklev, and W. Smith Chem. Phys. Lipids 144 2006 172