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Biosynthesis of 1-alkenes in the defensive secretions ofTribolium confusum (Tenebrionidae); stereochemical implications

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Summary

The terminally unsaturated hydrocarbons of the defensive secretion ofTribolium confusum are biosynthesized from fatty acids by oxidative decarboxylation. The process involves an enantiospecific cleavage of the C−H bond of thepro-(S) C(3)−H atom and simultaneous decarboxylation of the acid into an 1-alkene and carbon dioxide via ananti-periplanar transition state geometry (anti-elimination). The stereochemistry of this biotranformation is identical in all respects with the same reaction in higher plants. The mechanism seems to be of general importance for the biosynthesis of many vinylic substructures of natural products from oxygen-containing precursors.

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Authors and Affiliations

  1. Institut für Organische Chemie, Richard Willstätter-Allee, D-7500, Karlsruhe

    G. Görgen, C. Frößl & W. Boland

  2. Tierökologie II der Universität Bayreuth, Postf. 101251, D-8580, Bayreuth, Federal Republic of Germany

    K. Dettner

Authors
  1. G. Görgen
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  2. C. Frößl
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  3. W. Boland
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  4. K. Dettner
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Görgen, G., Frößl, C., Boland, W. et al. Biosynthesis of 1-alkenes in the defensive secretions ofTribolium confusum (Tenebrionidae); stereochemical implications. Experientia 46, 700–704 (1990). https://doi.org/10.1007/BF01939939

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  • DOI: https://doi.org/10.1007/BF01939939

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