Synthesis and Absolute Configuration of Rotundial, a Mosquito Repellent from the Leaves ofVitex rotundiforia

Abstract

The enantiomers of rotundial (1), a mosquito repellent from the leaves of Vitex rotundiforia, were synthesized from the enantiomers of limonene oxide (2). The absolute configuration of natural rotundial was determined to be R.

The Importance of Organocatalysis (Asymmetric and Non‐Asymmetric) in Agrochemicals

“…[31,7c] The yield of the final cyclization step (36 %, 86 % ee) was lessened due to the the sensitivity of rotundial to degradation. [32] The overall yield of 25 % compares favorably with earlier reported syntheses, [33] and the optical rotation was in agreement with the desired (R)-configuration (Scheme 9).…”

Repellency effect of forty-one essential oils against Aedes, Anopheles, and Culex mosquitoes

“…Repellency properties of nepetalactone (cyclopentanoid monoterpene) isolated from the catnip plant, Nepeta cataria, against 17 species of insects were reported by Eisner (1964). Also, many monoterpenes were reported for their insect repellent properties such as α-pinenen, limonene, terpinolene, citronellol, citronellal, camphor, rotundial, dolichodial, teucrein, and isoborneol (Perttunen 1957;Moore 1974;Takikawa et al 1998;Eisner et al 2000;Bläske et al 2003). Among 29 tested alkaloids obtained from Delphinium, Consolida, and Aconitum species, 21 compounds showed a promising insect repellent activity, while eight of them were not active.…”