A Concise Asymmetric Synthesis of (2<i>S</i>,3<i>S</i>,7<i>S</i>)-3,7-Dimethylpentadecan-2-yl Acetate and Propionate, the Sex Pheromones of Pine Sawflies
作者:Pei-Qiang Huang、Hong-Qiao Lan、Xiao Zheng、Yuan-Ping Ruan
DOI:10.1021/jo0497961
日期:2004.5.1
7S)-3,7-Dimethylpentadecan-2-yl acetate (2) and its propionate analogue (3) are the main sex pheromones of all Neodiprion species and Diprion similes, respectively. Starting from (S)-malic acid and employing a highly chemo-, regio-, and stereoselective tandem ester reduction−epoxide formation−reductive epoxide-opening reaction protocol, an efficient total synthesis of (2S,3S,7S)-2 and -3 is reported
(2 S,3 S,7 S)-3,7-乙酸二甲基十五烷-2-基酯(2)和其丙酸酯类似物(3)分别是所有新敌敌pr物种和敌敌畏类似物的主要性信息素。从(S)-苹果酸开始,采用高度化学,区域和立体选择性的串联酯还原反应-环氧化合物形成-还原性环氧化合物开放反应方案,可以有效地合成(2 S,3 S,7 S)-本文报道了图2和-3。