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Title:   Author  item
                                            LING, TAOTAO - University Of Californiaitem
                                            XU, JING - University Of Californiaitem
                                            SMITH, RYAN - University Of Californiaitem
                                            ALI, ABBAS - University Of Mississippiitem
                                            Cantrell, Charlesitem
                                            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.


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