Synthesis of the enantiomers of (3Z,9Z)-cis-6,7-epoxy-3,9-octadecadiene,one of the major components of the sex pheromone of Ectropis oblique Prout |
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Authors: | Jie Yu Feng Guo Yun-Qiu Yang Hui-Hui Gao Ru-Yan Hou Xiao-Chun Wan |
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Institution: | State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China |
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Abstract: | Both enantiomers of (3Z,9Z)-cis-6,7-epoxy-3,9-octadecadiene, one of which is the major component of the sex pheromone of Ectropis oblique Prout, were synthesized in 23% overall yield for the (?)-(6S,7R)-enantiomer and 18% yield for the (+)-(6R,7S)-isomer. This protocol uses a sequential regioselective ring-opening strategy and provides a convenient and reliable access to other structurally related insect sex pheromones. Preliminary biological studies revealed that (?)-(6S,7R)-2a was roughly as active as the natural pheromone, while racemic (±)-2 was less bioactive and (+)-2b was much less bioactive. |
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Keywords: | Corresponding author Tel /fax: +86 551 65786765 |
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