Abstract
The total syntheses of 9(Z),12(E)- and 9(E),12(Z)-octadecadienoic acids have been carried out. A useful intermediate in both syntheses, 8-bromo-octanoic acid, recently has become available from commercial sources. This compound has been used to expedite the preparation of these isomers. The remaining carbon atoms were derived from propargyl alcohol along with either 1-heptyne or acetylene and 1-bromopentane. Because the overall yield for each sequence was roughly 15% and there were no extraordinary reaction conditions in any of the synthetic steps, the compounds could be prepared readily in multiple gram quantities. The syntheses of the two compounds were supported by data from a variety of spectroscopic techniques.
Similar content being viewed by others
References
Dutton, H.J. (1979) inGeometrical and Positional Fatty Acid Isomers Emken, E.A., and Dutton, H.J., eds.) pp. 1–16, American Oil Chemists' Society, Champaign, IL.
Kritchevsky, D., Davidson, L.M., Weight, M., Kriek, N.P.J., and DuPlessis, J.P. (1984)Atherosclerosis 51, 123.
Hill, E.G., Johnson, S.B., Lawson, L.D., Hahfouz, M.M., and Holman, R.T. (1982)Proc. Natl. Acad. Sci. USA 79, 953–957.
Applewhite, T.H. (1983) inDietary Fats and Health (Perkins, E.G., and Visek, W.J., eds.), pp. 414–424, American Oil Chemists' Society, Champaign, IL.
Anderson, R.L., Fullmer, C.S., and Hollenbach, E.J. (1975)J. Nutr. 105, 393–400.
Ide, T., and Sugano, M. (1984)Biochim. Biophys. Acta 794, 281–291.
DeGaudemaris, M., and Agnaud, P. (1962)Bull. Soc. Chim. Fr. 28, 315–325.
Gunstone, F.D., and Jacobsberg, F.R. (1972)Chem. Phys. Lipids 9, 112–122.
Porter, N.A., and Wujek, D.G. (1984)J. Am. Chem. Soc. 106, 2626–2629.
Still, W.C., Kahn, M., and Mitra, A. (1978)J. Org. Chem. 43, 2923–2925.
Ames, D.E., Covell, A.N., and Goodburn, T.G. (1963)J. Chem. Soc. 5889–5893.
Dear, R.E.A., and Pattison, F.L.M. (1963)J. Am. Chem. Soc. 85, 622–626.
Carvalho, J.F., and Prestwich, D. (1984)J. Org. Chem. 49, 1251–1258.
Crombie, L. (1952)J. Chem. Soc., 4338–4346.
Naves, Y.R. (1943)Helv. Chim. Acta 26, 1998.
DeJarlais, W.J., and Emken, E.A. (1980)Synth. Commun. 10, 653–666.
Black, H.K., and Weedon, B.C.L. (1953)J. Chem. Soc., 1785–1793.
Gunstone, F.D., Pollar, M.R., Scrimgewr, C.M. and Vedanayagam, H.S. (1977)Chem. Phys. Lipids 18, 115–129.
Author information
Authors and Affiliations
About this article
Cite this article
Ofsuki, T., Brooker, R.F. & Funk, M.O. Two geometrical isomers of linoleic acid: Improved total syntheses. Lipids 21, 178–181 (1986). https://doi.org/10.1007/BF02534443
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02534443