Pheromone synthesis. Part 265: Synthesis and stereochemical composition of two pheromonal compounds of the female Korean apricot wasp, Eurytoma maslovskii

• Published in: Tetrahedron Vol. 76; no. 34; pp. 131410 - 131416
• Main Authors: Ohkubo, Yasutaka, Akasaka, Kazuaki, Masuda, Yui, Konishi, Shunsuke, Yang, Chang Yeol, Takikawa, Hirosato, Mori, Kenji
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 21.08.2020; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Enantioselective synthesis; Eurytoma maslovskii; Ohrui–Akasaka method; Pheromone; Physical Sciences; Science & Technology; Ohrui–Akasaka method; Eurytoma maslovskii; Pheromone; Enantioselective synthesis; Ohrui-Akasaka method; REAGENTS
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2020.131410

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, (2S,10R)-dimethyldodecyl propanoate, was also the most abundant component in the cuticular extract. [Display omitted] •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.