A Short and Stereoselective Synthesis of the Sex Pheromone of Bonagota cranaodes (Lepidoptera: Tortricidae)

Abstract

O acetato de (3E,5Z)-dodecadienila, feromônio sexual da lagarta enroladeira da maçã, Bonagota cranaodes (Lepidoptera: Tortricidae), foi estereosseletivamente sintetizado empregando-se uma metodologia envolvendo o acoplamento de Z-alquenil cuprato com 4-iodo-3-butin-1-ol, como etapa chave. A stereoselective synthesis of (3E,5Z)-dodecadienyl acetate, the sex pheromone of the leafroller moth Bonagota cranaodes, was efficiently carried out using a methodology based on the coupling of Z-alkenyl cuprate with 4-iodo-3-butyn-1-ol in the key step.

Synthesis and Field Test of Three Candidates for Soybean Pod Borer's Sex Pheromone

“…Air and water sensitive solutions were transferred using hypodermic syringes. The 1 H NMR and 13 C NMR spectroscopic data were recorded in CDCl 3 solution with either Bruker AM-200 or AM-400 MHz spectrometers. The chemical shifts are reported in δ (ppm) relative to TMS in CDCl 3 .…”

“…In recent years, these kinds of sex pheromones were also synthesized by the Suzuki-Miyaura crosscoupling reaction, but with costly palladium complex as catalyst [9,10]. Herein, we report a facile, cheap synthetic approach for these pheromone components based on the Li 2 CuCl 4 catalytic cross coupling reaction [11][12][13][14]. In this synthesis, we avoided the complicated geometrical isomer separation by using the commercially available substituted allylic alcohol with the same stereochemistry as the starting materials.…”

Insect pheromone synthesis in Brazil: an overview

“…74 Simonelli et al 75 described a stereoselective synthesis of this compound using methodology based on the coupling of a Z-alkenyl cuprate with 1-iodo-2-butyn-4-ol (46.8% overall yield)(Scheme 20).…”