Natural Product Communications ( IF 1.5 ) Pub Date : 2021-05-31 , DOI: 10.1177/1934578x211020149 Guo-Guo He 1 , Si-Fan Liu 2 , Bao-Qi Rao 2 , Hong-Jin Bai 1 , Zhen-Ting Du 2, 3
An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth, has been efficiently achieved. A key chiral intermediate, (R)−4-(benzyloxy)−3-methylbutanal, which has been developed as the resource chemical, can be obtained in large quantities from the steroid industry. 1,11-Undecanediol is selectively masked, and then converted into a phosphonium salt derivative, thereby effectively constructing a carbon skeleton. The target molecule is synthesized in 8 linear steps, with a 42% yield. The key characteristic of our synthesis lies in its chiral-pool strategy.
中文翻译:
( S )-14-Methyl-1-Octadecene 的一种新的不对称合成,桃叶潜蛾的性信息素
桃潜叶蛾的性信息素 14-methyl-1-octadecene 的不对称合成已被有效实现。一种关键的手性中间体( R )-4-(苄氧基)-3-甲基丁醛已被开发为资源化学品,可以从类固醇工业中大量获得。1,11-十一烷二醇被选择性掩蔽,然后转化为鏻盐衍生物,从而有效构建碳骨架。目标分子以 8 个线性步骤合成,产率为 42%。我们合成的关键特征在于其手性池策略。