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

Fabio Simonelli,Davi C Silva,Alfredo R.M Oliveira,Francisco A Marques

doi:10.1590/s0103-50531998000400009

Abstract

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.

Highlights

(3E,5Z)-3,5-dodecadienyl acetate was identified by Unelius C.R. et al as the sex pheromone of the leafroller Bonagota cranaodes (Lepidoptera: Tortricidae), an economically important insect pest of apples in Southern Brazil
The synthesis of (3E,5Z)-3,5-dodecadienyl acetate employing the coupling of the Z-alkenyl cuprate 13,4,5 with the alkynol iodide 26, the key step of the process, is outlined in Scheme 1
The enynol 3 was reduced stereoselectively with lithium aluminum hydride[7,8] in diglyme[9] affording the desired (E,Z)-dienol which was acetylated in pyridine/acetic anhydride, leading to the preparation of the pheromone in 46,8% overall yield

Summary

Introduction

(3E,5Z)-3,5-dodecadienyl acetate was identified by Unelius C.R. et al as the sex pheromone of the leafroller Bonagota cranaodes (Lepidoptera: Tortricidae), an economically important insect pest of apples in Southern Brazil. In order to elucidate the pheromone structure this compound was first prepared by a methodology in low stereoselectivity and yield[1]. We describe a short and stereoselective synthesis of this pheromone in three steps with 46,8% overall yield.

Results

Conclusion