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Insect pheromones and their analogues XLIII. Chiral pheromones from (S)-(+)-3,7-dimethylocta-1,6-diene 3. Synthesis of (4R)-4-methylnonan-1-OL — Sex pheromone of Tenebrio molitor and its racemic analogue

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Abstract

Starting from the readily available enantiomerically enriched (S)-(+)-3,7-dimethylocta-1,6-diene (ee ≃ 50%), we have synthesized (4R)-4-methylnonan-1-ol — the sex pheromone of the yellow mealworm bettleTenebrio molitor L. A scheme for synthesizing the racemic analogue of the pheromone from 4-methyltetrahydropyran has been developed.

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Authors
  1. V. N. Odinokov
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  2. G. Yu. Ishmuratov
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  3. M. P. Yakovleva
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  4. O. V. Sokol'skaya
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  5. R. Ya. Kharisov
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  6. É. P. Serebryakov
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  7. G. A. Tolstikov
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Additional information

Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 711–714, November–December, 1992.

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Odinokov, V.N., Ishmuratov, G.Y., Yakovleva, M.P. et al. Insect pheromones and their analogues XLIII. Chiral pheromones from (S)-(+)-3,7-dimethylocta-1,6-diene 3. Synthesis of (4R)-4-methylnonan-1-OL — Sex pheromone of Tenebrio molitor and its racemic analogue. Chem Nat Compd 28, 618–621 (1992). https://doi.org/10.1007/BF00630443

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  • DOI: https://doi.org/10.1007/BF00630443

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