The geometric isomers of methyl-2,4,6-decatrienoate, including pheromones of at least two species of stink bugs
2005
Khrimian, Ashot
All eight geometric isomers of methyl 2,4,6-decatrienoate were synthesized from readily accessible starting materials by fully exploiting Wittig-type olefinations, and taking advantage of an easy separation of 2E and 2Z unsaturated esters. The aggregation pheromone of the brown-winged green bug, Plautia stali, methyl (E,E,Z)-2,4,6-decatrienoate (also a cross-attractant for the brown marmorated stink bug, Halyomorpha halys), was expediently produced in two easy steps from (E)-4,4-dimethoxy-2-butenal in 55% yield. The sex pheromone of the red-shouldered stink bug, Thyanta pallidovirens, methyl (E,Z,Z)-2,4,6-decatrienoate, was conveniently synthesized from 2,4-octadiyn-1-ol in 32% yield using in situ manganese dioxide oxidation–Wittig condensation in a key step. All eight stereoisomers of methyl 2,4,6-decatrienoate, among them sex pheromones of stink bugs, were synthesized by fully exploiting Wittig-type olefinations, including in situ MnO2 oxidation-Wittig reaction.
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