Concise Preparation of the (3E,5Z)-Alkadienyl System. New Approach to the Synthesis of Principal Insect Sex Pheromone Constituents

A new rapid and low-cost preparation of the (3E,5Z)-3,5-alkadienyl system, encountered in several insect pheromone constituents, was developed. Knoevenagel condensation of (E)-2-alkenals with ethyl hydrogen malonate in dimethyl sulfoxide, in the presence of a catalytic amount of piperidinium acetate...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2004-08, Vol.52 (16), p.5047-5051
Main Authors: Ragoussis, Valentine, Panopoulou, Maria, Ragoussis, Nikitas
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
Animals
Biological and medical sciences
chemical reactions
Control
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
Hydrogen Bonding
insect pests
Insecta
Insecta - chemistry
Integrated pest control
Magnetic Resonance Spectroscopy
Molecular Structure
Phytopathology. Animal pests. Plant and forest protection
plant pests
Protozoa. Invertebrates
Sex Attractants - chemical synthesis
sex pheromones
synthesis
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Summary:A new rapid and low-cost preparation of the (3E,5Z)-3,5-alkadienyl system, encountered in several insect pheromone constituents, was developed. Knoevenagel condensation of (E)-2-alkenals with ethyl hydrogen malonate in dimethyl sulfoxide, in the presence of a catalytic amount of piperidinium acetate, led to a mixture of geometrical isomers of ethyl 3,5-alkadienoates and ethyl 2,4-alkadienoates, from which the (3E,5Z)-3,5-alkadienoate was conveniently separated, by the use of urea inclusion complex formation. The importance of this procedure has been illustrated by the preparation of the (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) 1, the (3E,5Z)-3,5-dodecadienyl acetate 2, and the (3E,5Z)-3,5-tetradecadienyl acetate 3. These compounds are the main components of insect sex pheromones and constitute synthetic targets of considerable interest for the semiochemical community. Keywords: Knoevenagel condensation; pheromone synthesis; semiochemicals; megatomoic acid; Attagenus megatoma; Bonagota cranaodes; Recurvaria leucatella
ISSN:0021-8561
1520-5118
DOI:10.1021/jf049406b