Work

Modular Stereoselective Synthesis of Sex Pheromone of Lambdina fiscellaria lugubrosa (Hulst) and Discovery of Cross-Species Attraction in Semiothisa cinerearia (Bremer & Grey)

Year: 2025

Type: article

Abstract: The western hemlock looper, Lambdina fiscellaria lugubrosa (Hulst) is a destructive defoliator of coniferous forests and a major cause of economic losses in forestry. A novel and efficient stereoselective synthesis of the sex pheromone of the western hemlock looper (1, 2 and 3) has been successfully achieved. The synthetic strategy integrates several key transformations, including Evans’ chiral auxiliaries, Grignard cross-coupling, hydroboration–oxidation, sulfone alkylation, and hydrogenation, providing an efficient and scalable approach for sex pheromone production. The three synthesized pheromone components were subsequently tested for their ability to attract Semiothisa cinerearia (Bremer & Grey) using both Y-tube and cage bioassays. Notably, compound 1 exhibited a cross-species attractive effect on S. cinerearia, a species that had not previously been documented to respond to the pheromone of L. fiscellaria lugubrosa. This discovery underscores the potential for cross-species attraction, broadens our understanding of pheromone specificity, and emphasizes the value of stereoselectively synthesized pheromones as molecular tools for cross-species pest monitoring and integrated pest management.

Source: Molecules

DOI: 10.3390/molecules30214216