滚动新闻:
    科研成果
    您现在的位置是:首页 > 科学研究 > 科研成果

    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:2017-06-26
    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.