A novel synthesis of (−)-callicarpenal

Daichi Oguro, Naoki Mori, Hirosato Takikawa, Hidenori Watanabe

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Callicarpenal, isolated from the leaves of American beautyberry (Callicarpa americana) and Japanese beautyberry (Callicarpa japonica), exhibits significant mosquito bite-deterring activity and repellent activity against ticks and fire ants. The mosquito bite-deterring activity level of callicarpenal was reported to be similar to that of N,N-diethyl-m-toluamide. The novel synthesis of (−)-callicarpenal reported herein was accomplished by starting from (+)-pulegone. In our original approach, a novel Prins-type cyclization based on Meyer–Schuster rearrangement was featured as a key step.

Original languageEnglish
Pages (from-to)5745-5751
Number of pages7
JournalTetrahedron
Volume74
Issue number39
DOIs
Publication statusPublished - 2018 Sep 27
Externally publishedYes

Keywords

  • Callicarpenal
  • Meyer-Schuster rearrangement
  • Mosquito repellent
  • Prins reaction
  • Pulegone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Oguro, D., Mori, N., Takikawa, H., & Watanabe, H. (2018). A novel synthesis of (−)-callicarpenal. Tetrahedron, 74(39), 5745-5751. https://doi.org/10.1016/j.tet.2018.08.012