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Title: Synthesis of (-)-callicarpenal a natural arthropod-repellent terpenoid

Author
item LING, TAOTAO - University Of California
item XU, JING - University Of California
item SMITH, RYAN - University Of California
item ALI, ABBAS - University Of Mississippi
item Cantrell, Charles
item THEODORAKIS, EMMANUEL - University Of California

Submitted to: Tetrahedron
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/25/2011
Publication Date: 3/4/2011
Citation: Ling, T., Xu, J., Smith, R., Ali, A., Cantrell, C.L., Theodorakis, E.A. 2011. Synthesis of (-)-callicarpenal a natural arthropod-repellent terpenoid. Tetrahedron. 67:3023-3029.

Interpretive Summary: Callicarpenal, a natural compound extracted from the American beautyberry (Callicarpa americana) plant, has shown significant repellent activity against mosquitoes, ticks and imported fire ants. Here we report an efficient synthetic approach to this natural product due to the commercial interest in producing this compound in larger quantities and to aid in the understanding of the relationship between the chemical structure of callicarpenal and its repellent activity. Along these lines, we also present results of the mosquito biting deterrence effects of callicarpenal, as well as its synthetic precursors and related C8-epi-isomers.

Technical Abstract: Callicarpenal, a natural terpenoid extracted from American beautyberry (Callicarpa americana), has shown significant repellent activity against mosquitoes, ticks and imported fire ants. Here we report an efficient synthetic approach to this natural product. We also present results of the mosquito biting deterrence effects of callicarpenal, as well as its synthetic precursors and related C8-epi-isomers.