Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing 100091, China.
J Asian Nat Prod Res. 2022 Jun;24(6):569-576. doi: 10.1080/10286020.2020.1839433. Epub 2020 Dec 14.
-(-)--Verbenol () and its antipode, -(+)--verbenol () have been confirmed as the critical pheromone components of bark beetles. Synthesis of these two active secondary alcohols ( and ) from commercially available starting materials --pinene and --pinene was reported. The key steps were mainly depended on the effective S2 stereo-inversion of the hydroxy group of sterically hindered alcohols ( and '), using Mitsunobu reaction or hydrolysis of mesylate ester, alternatively. Our results provide a new and stereo-selectivity way to obtain optically active insect pheromones.
(-)-马鞭烯醇（）及其对映体(+)-马鞭烯醇（）已被确认为树皮甲虫的关键信息素成分。这两种活性仲醇（和）已由商业上可获得的起始原料——蒎烯和莰烯合成。关键步骤主要依赖于空间位阻醇（和‘）羟基的有效 S2 立体反转，使用 Mitsunobu 反应或甲磺酸酯的水解来替代。我们的结果提供了一种获得光学活性昆虫信息素的新的和立体选择性的方法。
