Pheromone synthesis. Part 261: Synthesis of four pyrazines produced by females of the Korean apricot wasp, Eurytoma maslovskii
2017
Mori, Kenji | Yang, Chang Yeol
Four pyrazines were synthesized as sex specific volatiles of female Korean apricot wasp, Eurytoma maslovskii. They are 2,5-dimethyl-3-vinylpyrazine (1), 2,5-dimethyl-3-(2-methylpropyl)pyrazine (2), 2,5-dimethyl-3-(2-methylbutyl)pyrazine (3), and 2,5-dimethyl-3-(3-methylbutylpyrazine (4). They were synthesized in 74–85% yields by Pd- or Fe-catalyzed cross-coupling reactions between 3-chloro-2,5-dimethylpyrazine and CH2=CHBF3K or RMgBr. The present synthesis of 1 is the most reliable and scalable one to date.
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