- The geometric isomers of methyl-2,4,6-decatrienoate, including pheromones of at least two species of stink bugs
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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.
- Khrimian, Ashot
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p. 3651 - 3657
(2007/10/03)
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- Methyl (2E,4Z,6Z)-deca-2,4,6-trienoate, a thermally unstable, sex-specific compound from the stink bug Thyanta pallidovirens
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Sexually mature male stink bugs, Thyanta pallidovirens, release a male-specific blend of volatiles, including several sesquiterpene hydrocarbons, and the highly conjugated ester methyl (2E,4Z,6Z)-deca-2,4,6-trienoate 1. The latter compound was synthesized, and found to rearrange under GC conditions via a 1,7 sigmatropic rearrangement.
- Millar, Jocelyn G.
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p. 7971 - 7972
(2007/10/03)
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