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Abstracts - Adeildo Junior de Oliveira

SYNTHESIS OF THE SEX PHEROMONE OF THE PLODIA INTERPUNCTELLA

 Adeildo Junior de Oliveira1*, Antônio Euzébio Goulart Santana2, Henrique Fonseca Goulart3

1 adeildojro@gmail.com

2 aegsal@gmail.com

3 fonsecagoulart@gmail.com

* Correspondence: adeildojro@gmail.com

Plodia interpunctella, known as indian meal moth, is an important pest that attacks grains stored in Brazil and other regions of the world. Her sex pheromone was identified as Z9,E12-tetradecadienyl acetate. The pheromone was synthesized according to the synthetic route below, including a step of preparing of the haloalcohol 2 from the corresponding diol (1). The product of this step was converted to the corresponding acetal (3). The compound 3 was reacted with lithium acellite in DMSO to give compound 4, which was coupled with crotyl bromide, obtaining intermediate 5. The alcohol 6 was obtained by treatment of 5 in methanol and p- toluenesulfonic acid. The product 6 was stirred with Lindlar catalyst in methanol in the presence of hydrogen to obtain the alkene 7 which was acetylated, resulting in compound 8, acetato de Z9,E12-tetradecadienila (P. interpunctella pheromone).

Refs.

  1. Kuwahara, Y. et al., Science. 171:801-802, 1971a.