Pheromone synthesis. Part 265: Synthesis and stereochemical composition of two pheromonal compounds of the female Korean apricot wasp, Eurytoma maslovskii. Issue 34 (21st August 2020)

• Record Type: Journal Article
• Authors: Ohkubo, Yasutaka; Akasaka, Kazuaki; Masuda, Yui; Konishi, Shunsuke; Yang, Chang Yeol; Takikawa, Hirosato; Mori, Kenji
• Is Part Of: Tetrahedron. Volume 76:Issue 34(2020)
• Publication Date: 2020-08-21
• Subjects: Eurytoma maslovskii -- Pheromone -- Enantioselective synthesis -- Ohrui–Akasaka method; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131410
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 2, 10-Dimethyldodecyl propanoate and 2, 8-dimethyldecyl propanoate are two pheromonal compounds secreted by the female Korean apricot wasp, Eurytoma maslovskii . The enantioselective synthesis of all the stereoisomers of both components was conducted; HPLC analysis based on the chiral derivatization method (Ohrui–Akasaka method) was applied for the clarification of the stereochemical composition of these two components. The most pheromonally active compound, (2 S, 10 R )-dimethyldodecyl propanoate, was also the most abundant component in the cuticular extract. Graphical abstract: Image 1 Highlights: Two pheromone candidates of Eurytoma maslovskii were synthesized. The non-stereoselective and enantioselective synthesis of these two compounds was achieved. The total composition of the naturally occurring pheromone was confirmed by HPLC analysis. Ohrui-Akasaka method was crucial for the analysis of the natural pheromone.