| Title: | Stereospecific synthesis of S-(-)-trans-verbenol and its antipode by inversion of sterically hindered alcohols |
| Author(s): | Liu F; Fang JX; Kong XB; Zhang SF; Zhang Z; |
| Address: | "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" |
| DOI: | 10.1080/10286020.2020.1839433 |
| ISSN/ISBN: | 1477-2213 (Electronic) 1028-6020 (Linking) |
| Abstract: | "S-(-)-trans-Verbenol (1) and its antipode, R-(+)-trans-verbenol (1') have been confirmed as the critical pheromone components of bark beetles. Synthesis of these two active secondary alcohols (1 and 1') from commercially available starting materials S-alpha-pinene and R-alpha-pinene was reported. The key steps were mainly depended on the effective S(N)2 stereo-inversion of the hydroxy group of sterically hindered alcohols (3 and 3'), using Mitsunobu reaction or hydrolysis of mesylate ester, alternatively. Our results provide a new and stereo-selectivity way to obtain optically active insect pheromones" |
| Keywords: | *Alcohols Animals Bicyclic Monoterpenes Molecular Structure Pheromones *Weevils Mitsunobu reaction R-(+)-trans-verbenol S-(-)-trans-verbenol SN2 inversion sterically hindered alcohols; |
| Notes: | "MedlineLiu, Fu Fang, Jia-Xing Kong, Xiang-Bo Zhang, Su-Fang Zhang, Zhen eng England 2020/12/15 J Asian Nat Prod Res. 2022 Jun; 24(6):569-576. doi: 10.1080/10286020.2020.1839433. Epub 2020 Dec 14" |
