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1. Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones

Author

E. A. Matiushenkov, Dzmitry M. Zubrytski, and Dzmitry G. Kananovich

Subjects
chemistry.chemical_classification, biology, Bicyclic molecule, Double bond, 010405 organic chemistry, Chemistry, Stereochemistry, Organic Chemistry, Insect pheromones, 010402 general chemistry, biology.organism_classification, 01 natural sciences, Tortrix viridana, 0104 chemical sciences, chemistry.chemical_compound, Sex pheromone, Tuta absoluta, Rhyacionia buoliana, Benzene
Abstract

Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).

Published
2017
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