Stereoselective synthesis of 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane, and 5,9-dimethylheptadecane, the sex pheromones of female apple leafminer |
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Authors: | Jhillu S. Yadav Kamakolanu Uma Gayathri Neetipalli Thrimurtulu Attaluri R. Prasad |
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Affiliation: | Pheromone Group, Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, Andhra Pradesh, India |
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Abstract: | The stereoselective synthesis of (10R,14R)-10,14-dimethyloctadec-1-ene (1), (5R,9R)-5,9-dimethyloctadecane (2), and (5R,9R)-5,9-dimethylheptadecane (3) the sex pheromone components of female apple leafminer was accomplished by reductive elimination tosyl and isonitrile groups of dialkylated tosylmethyl isonitrile. The key steps involved were dialkylation of TosMIC with 1-iodo 2-methyl alkanes, which were derived from Evan's alkylation of chiral auxiliary and subsequent reduction. |
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Keywords: | Apple leafminer pheromone Chiral auxiliary Evans alkylation TosMIC alkylation and reduction |
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