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Synthesis of the Toxic Principle of Dichapetalum toxicarium (18-Fluoro-cis-9-Octadecenoic Acid)

Naturevolume 192pages12841285 (1961) | Download Citation



Dichapetalum toxicarium (Chailletia toxicaria, Don). a shrub occurring in Sierra Leone, produces a hard and woody fruit which is extremely toxic to warm-blooded animals. The pharmacological, medical, and historical aspects of this plant have recently been reviewed1. Peters and colleagues have concluded2, on the basis of nuclear magnetic resonance, infra-red spectroscopy and ozonolysis, that the toxic principle is 18-fluoro-cis-9-octadecenoic acid (ω-fluoro-oleic acid), F(CH2)8CH=CH(CH2)7COOH. It was in order to confirm this conclusion that the following synthesis of ω-fluoro-oleic acid was undertaken:

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  1. 1

    Pattison, F. L. M., Toxic Aliphatic Fluorine Compounds, 83 (Elsevier Pub. Co., Amsterdam, 1959).

  2. 2

    Peters, R. A., Hall, R. J., Ward, P. F. V., and Sheppard, N., Biochem. J., 77, 17 (1960).

  3. 3

    Pattison, F. L. M., and Howell, W. C., J. Org. Chem., 21, 748 (1956).

  4. 4

    Pattison, F. L. M., and Norman, J. J., J. Amer. Chem. Soc., 79, 2311 (1957).

  5. 5

    Pattison, F. L. M., Stothers, J. B., and Woolford, R. G., J. Amer. Chem. Soc., 78, 2255 (1956).

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  1. Department of Chemistry, University of Western Ontario, London, Ontario

    • F. L. M. PATTISON
    •  & R. E. A. DEAR


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