Synthesis of (-)-callicarpenal, a Potent Arthropod Repellent

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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Document Details

Document Type
Technical Report
Publication Date
Jan 01, 2011
Accession Number
ADA544464

Entities

People

  • Abbas Ali
  • Charles L. Cantrell
  • Emmanuel A. Theodorakis
  • Jing Xu
  • Ryan Smith
  • Taotao Ling

Organizations

  • University of California, San Diego

Tags

DTIC Thesaurus Topics

  • Alcohols
  • Alkenes
  • Analogs
  • Bioassay
  • Biochemistry
  • Biological Products
  • Chemical Synthesis
  • Chemistry
  • Chromatography
  • Column Chromatography
  • Dengue
  • Ethers
  • Insect Repellents
  • Ketones
  • Organic Chemistry
  • Plastic Explosives
  • X Rays

Fields of Study

  • Chemistry

Readers

  • Molecular and Cellular Biochemistry
  • Vector-Borne Disease and Entomology
  • Wetland-Land-Environmental Management.