Synthesis of the enantiomers of (3Z, 9Z)-cis-6, 7-epoxy-3, 9-octadecadiene, one of the major
 
作者: 文章来源: 点击数: 更新日期:2017-05-31
Title

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

Authors

Jie Yu†, Feng Guo†, Yun-Qiu Yang, Hui-Hui Gao, Ru-Yan Hou, Xiao-Chun Wan*

Journal

Tetrahedron: Asymmetry, https://doi.org/10.1016/j.tetasy.2017.04.010

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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  • synthesis of the enantiomers of (3z,9z)(俞杰,郭峰,宛晓春,2017).pdf
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