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Published on: August 22, 2018
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Synthesis of (±)-disparlure
J H Markgraf1, S I Lusskin, E C McDonald
1Department of Chemistry, Williams College, 01267, Williamstown, Massachusetts.
Journal of Chemical Ecology
|January 11, 2014
Summary
A new six-step synthesis creates disparlure, the gypsy moth
Area of Science:
- Organic Chemistry
- Insect Chemical Ecology
Background:
- Disparlure is the sex pheromone of the gypsy moth.
- Effective pest control strategies are crucial for managing gypsy moth populations.
Purpose of the Study:
- To develop an efficient synthetic route for racemic disparlure.
- To provide a reliable method for producing gypsy moth pheromone for research and application.
Main Methods:
- A convergent synthesis approach was employed.
- The key step involved a Wittig reaction between 6-methylheptanal and triphenylundecylphosphonium bromide.
- Potassium carbonate and a crown ether were used as reagents.
Main Results:
- A six-step synthesis for racemic (Z)-7,8-epoxy-2-methyloctadecane (disparlure) was successfully developed.
- The synthesis utilizes a crucial Wittig reaction for efficient coupling.
- The method provides a viable pathway to the gypsy moth sex pheromone.
Conclusions:
- The developed six-step synthesis offers an effective route to disparlure.
- This synthesis is valuable for gypsy moth management strategies.
- Further optimization may enhance yield and stereoselectivity.
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