A novel synthesis of (−)-callicarpenal. Issue 39 (27th September 2018)

• Record Type: Journal Article
• Authors: Oguro, Daichi; Mori, Naoki; Takikawa, Hirosato; Watanabe, Hidenori
• Is Part Of: Tetrahedron. Volume 74:Issue 39(2018)
• Page Start: 5745
• Page End: 5751
• Publication Date: 2018-09-27
• Subjects: Callicarpenal -- Prins reaction -- Meyer-Schuster rearrangement -- Mosquito repellent -- Pulegone; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.08.012
• Languages: English
• ISSNs: 0040-4020

Abstract

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. Graphical abstract: Image 1 Highlights: A novel synthesis of (−)-callicarpenal was achieved. Callicarpenal is a tetranorditerpene aldehyde with a potent mosquito repellent activity. Prins-type cyclization based on Meyer-Schuster rearrangement was featured as a key step.