Letter | Published:

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

Nature volume 192, pages 12841285 (30 December 1961) | Download Citation

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Abstract

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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References

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    , Toxic Aliphatic Fluorine Compounds, 83 (Elsevier Pub. Co., Amsterdam, 1959).

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    , , , and , Biochem. J., 77, 17 (1960).

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    , and , J. Org. Chem., 21, 748 (1956).

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    , and , J. Amer. Chem. Soc., 79, 2311 (1957).

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Author information

Affiliations

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

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

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DOI

https://doi.org/10.1038/1921284a0

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