Synthesis of (4R)-Methylnonan-1-ol and (4R,8RS)-Dimethyldecanal from (S)-(+)-3,7-Dimethyl-1,6-octadiene |
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| Authors: | G Yu Ismuratov M P Yakovleva A V Galyautdinova G A Tolstikov |
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| Institution: | (1) Russian Academy of Sciences, Institute of Organic Chemistry, Ufa Scientific Center, 450054 Ufa, pr. Oktyabrya, 71 |
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| Abstract: | Optically active (4R,8RS)-dimethyldecanal, an analog of the aggregation pheromone of the flour beetles Tribolium confusum and T. Castaneum, and (4R)-methylnonan-1-ol, the sex pheromone of the yellow mealworm Tenebrio molitor L., are synthesized using ozonolytic transformation of (6R,10)-dimethyl-9-undecen-2-one to (6R)-methyl-9-hydroxynonan-2-one in the key step. The starting compound is available as enantiomerically enriched (ee ~50%) (S)-(+)-3,7-dimethyl-1,6-octadiene. |
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| Keywords: | pheromone (4R)-methylnonanol (4R 8RS)-dimethyldecanal (S)-(+)-dihydromyrcene (6R 10)-dimethyl-9-yndecen-2-one (6R)-methyl-9-hydroxynonan-2-one sodium trisacetoxyborohydride synthesis |
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