# Synthesis of the aggregation pheromone of Tribolium castaneum

**Authors:** Biyu An, Xueyang Wang, Ao Jiao, Qinghua Bian, Jiangchun Zhong

PMC · DOI: 10.3762/bjoc.21.38 · 2025-03-06

## TL;DR

Scientists developed a new method to synthesize the aggregation pheromone of the red flour beetle, which could help in pest control.

## Contribution

A novel synthetic strategy for the aggregation pheromone of Tribolium castaneum is introduced.

## Key findings

- A new synthesis method involving ring-opening and stereospecific inversion was developed.
- The pheromone was successfully synthesized using Li2CuCl4-catalyzed coupling and oxidation.
- The method is effective for preparing the aggregation pheromone of Tribolium castaneum.

## Abstract

Tribolium castaneum Herbst is a destructive stored product pest. The aggregation pheromone of this pest was prepared via a new and effective strategy. The key steps include the ring-opening reaction of chiral 2-methyloxirane, the stereospecific inversion of chiral secondary tosylate, Li2CuCl4-catalyzed coupling of tosylate with Grignard reagent, and oxidation with RuCl3/NaIO4.

## Linked entities

- **Chemicals:** Li2CuCl4 (PubChem CID 11074879), RuCl3 (PubChem CID 61850), NaIO4 (PubChem CID 23667635)
- **Species:** Tribolium castaneum (taxon 7070)

## Full-text entities

- **Chemicals:** RuCl3 (MESH:C038365), 2-methyloxirane (-), Li2CuCl4 (MESH:C079759)
- **Species:** Tribolium castaneum (red flour beetle, species) [taxon 7070]

## Figures

5 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11897649/full.md

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Source: https://tomesphere.com/paper/PMC11897649