A Simple and Short Synthesis of Z-6-Heneicosen-11-One and Z-1,6-Heneicosen-11-One,The Sex Pheromones of Douglas-Fir Tussock Moth |
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Authors: | G. Bhaskar Reddy R. B. Mitra |
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Affiliation: | National Chemical Laboratory , Pune, 411 008, India |
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Abstract: | Z-6-Heneicosen-11-one (1) and Z-1,6-Heneicosen-11-one (2) are the sex pheromones of the Douglas-Fir Tussock moth, ‘Orgyia Pseudo Sugata’, isolated1,2 in 1975 and 1978 respectively. In contrast with other lepidopterous pheromones, which are unsaturated C12-C14 primary alcohols or acetates, these were found to be C21 ketones. The Douglas-Fir Tussock moth is a severe defoliator of the Fir forest; consequently, considerable interest attends the synthesis of these two pheromones. A number of syntheses of these two pheromones have been reported3 amongst which is one of our synthesis using N,N-dimethyl acetone 4 hydrazone as key intermediate. |
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