Synthesis of (-)-callicarpenal, a potent arthropod-repellent |
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Authors: | Ling Taotao Xu Jing Smith Ryan Ali Abbas Cantrell Charles L Theodorakis Emmanuel A |
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Institution: | a Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA b National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA c United States Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University, MS 38677, USA |
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Abstract: | Callicarpenal (1), a natural terpenoid isolated from American beautyberry (Callicarpa americana), has shown significant repellent activities against mosquitoes, ticks, and imported fire ants. Here we report our efficient synthetic approach to this natural product, and preliminary results of the mosquito biting-deterrent effects of callicarpenal as well as its synthetic precursors and related C8-epimers. The synthetic strategy allows rapid access to various epimers and analogues of the natural product that can be used to explore its structure-activity relationship and optimize its biological properties. |
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Keywords: | Arthropod repellent Arthropod-borne disease Natural products Callicarpenal Asymmetric synthesis |
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