Total synthesis of 3,4-epoxy-6,9-heneicosadiyne, sex pheromone component of Thyrinteina arnobia

Total synthesis of 3,4-epoxy-6,9-heneicosadiyne, sex pheromone component of Thyrinteina arnobia

Paiva, Marcelo M. de; Neppe, Tiago; Corrêa, Arlene G.

Abstract:

The Brazilian eucalyptus brown looper, Thyrinteina arnobia (Lepidoptera: Geometridae), is the most harmful of the Eucalyptus pests in Brazil, causing severe losses in wood production through defoliation. However, no practical and environmentally acceptable method of control currently exists. T. arnobia virgin female gland extract was analyzed by GC-EAD and two compounds elicited a strong and reproducible antennal response. GC-MS analyses suggested homoconjugated epoxydiene derivatives as sex pheromone compounds, being the main component identified as 3,4-epoxy-6,9-heneicosadiyne (1).In this work we describe the racemic and the studies towards the asymmetric synthesis epoxydiyne 1.

The Brazilian eucalyptus brown looper, Thyrinteina arnobia (Lepidoptera: Geometridae), is the most harmful of the Eucalyptus pests in Brazil, causing severe losses in wood production through defoliation. However, no practical and environmentally acceptable method of control currently exists. T. arnobia virgin female gland extract was analyzed by GC-EAD and two compounds elicited a strong and reproducible antennal response. GC-MS analyses suggested homoconjugated epoxydiene derivatives as sex pheromone compounds, being the main component identified as 3,4-epoxy-6,9-heneicosadiyne (1).In this work we describe the racemic and the studies towards the asymmetric synthesis epoxydiyne 1.

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DOI: 10.5151/chempro-14bmos-R0125-1

Referências bibliográficas

• [1] 1 Moreira, J. A. Ph.D. Thesis, PPG, UFSCar, 2003.
• [2] 2 Bell, T. W.; Ciaccio, J. A.; Tetrahedron Lett. 1988, 29, 865.
• [3] 3 Zhang, Z. -B. et al. Tetrahedron: Asymmetry 1999, 10, 837.
• [4] 4 Khrimian, A. et al. J. Agric. Food Chem. 2004, 52, 2890.

Como citar:

Paiva, Marcelo M. de; Neppe, Tiago; Corrêa, Arlene G.; "Total synthesis of 3,4-epoxy-6,9-heneicosadiyne, sex pheromone component of Thyrinteina arnobia", p-125-125. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0125-1