Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth
Yun Zhou, Jianan Wang, Beijing Tian, Yanwei Zhu, Yujuan Zhang, Jinlong Han, Jiangchun Zhong, Chenggang Shan
TL;DR
Scientists developed an efficient method to synthesize sex pheromones of two moths, which could help in pest control.
Contribution
A new asymmetric synthesis method for producing sex pheromones of elm spanworm and painted apple moth with high enantiomeric purity.
Findings
The sex pheromone of the elm spanworm was synthesized in 31% total yield.
The sex pheromones of the painted apple moth were synthesized in 26% and 32% total yields.
The final products achieved enantiomeric excess (ee) values up to 99%.
Abstract
A concise synthesis of the sex pheromones of elm spanworm as well as painted apple moth has been achieved. The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown’s P2-Ni reduction. This approach provided the sex pheromone of the elm spanworm (1) in 31% total yield and those of the painted apple moth (2, 3) in 26% and 32% total yields. The ee values of three final products were up to 99%. The synthesized pheromones hold promising potential for use in the management and control of these pests.
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Taxonomy
TopicsInsect Pheromone Research and Control · Neurobiology and Insect Physiology Research · Insect-Plant Interactions and Control