Concise syntheses of insect pheromones using Z-selective cross metathesis

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Insect Chemical Ecology

Background:

• Lepidopteran pheromones are vital for integrated pest management strategies.
• Efficient synthesis of Z-olefins, key components of many pheromones, remains a synthetic challenge.

Purpose of the Study:

• To report concise synthetic routes for nine cis-olefin-containing lepidopteran pheromones.
• To demonstrate the utility of ruthenium-based Z-selective cross metathesis for pheromone synthesis.

Main Methods:

• Ruthenium-catalyzed Z-selective cross metathesis.
• Multi-step organic synthesis to construct complex pheromone structures.

Main Results:

• Successfully synthesized nine distinct cis-olefin pheromones with diverse functionalities.
• Included the synthesis of an unconjugated (E,Z)-diene-containing pheromone.
• Achieved high efficiency and selectivity using the Z-selective cross metathesis.

Conclusions:

• Ruthenium-based Z-selective cross metathesis provides an efficient and advantageous method for synthesizing lepidopteran pheromones.
• This approach simplifies the preparation of Z-olefins compared to traditional methods.
• The developed routes are valuable for the scalable production of pheromones for pest control applications.