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. 2025 Mar 6:21:510-514.
doi: 10.3762/bjoc.21.38. eCollection 2025.

Synthesis of the aggregation pheromone of Tribolium castaneum

Biyu An  1 , Xueyang Wang  1 , Ao Jiao  2 , Qinghua Bian  1 , Jiangchun Zhong  1
Affiliations

Synthesis of the aggregation pheromone of Tribolium castaneum

Biyu An et al. Beilstein J Org Chem. .

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.

Keywords: aggregation pheromone; chiral 2-methyloxirane; red flour beetle; total synthesis.

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Figures

Figure 1
Figure 1
The aggregation pheromone of Tribolium castaneum.
Scheme 1
Scheme 1
Retrosynthetic analysis of the aggregation pheromone (4R,8R)-1.
Scheme 2
Scheme 2
Synthesis of chiral tosylate (S)-10.
Scheme 3
Scheme 3
Synthesis of chiral tosylate (R)-10.
Scheme 4
Scheme 4
Synthesis of the aggregation pheromone of Tribolium castaneum.
See this image and copyright information in PMC

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