Synthesis of (1<i>R</i>,7<i>Z</i>)-1-Methyl-7-hexadecenyl Acetate, the Female Sex Pheromone of the Honey Locust Gall Midge

Shikichi, Yasumasa; Mori, Kenji

doi:10.1271/bbb.120265

Cited by 2 publications

(1 citation statement)

References 9 publications

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“…This route has considerably improved for the preparation of large amounts of both the stereospecific and racemic OWBM pheromones for field trap applications, which can meet the demand to monitor, manage and control the sudden burst of OWBMs. In addition, some gall midge sex pheromones share similar structural characteristics 21–23,27,34 . Accordingly, this modular method can be readily modified for the synthesis of other sex pheromones.…”

Section: Discussionmentioning

confidence: 99%

Modular synthesis of the pheromone (2S,7S)‐2,7‐nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae)

et al. 2022

Pest Management Science

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BACKGROUND: Sudden outbreaks of the orange wheat blossom midge, Sitodiplosis mosellana (Géhin) cause huge wheat yield losses. Use of sex pheromones is more efficient than laborious egg counting to monitor these hidden-concealed insects. Quick synthesis of the sex pheromones is therefore required to meet the sudden outbreak needs. RESULTS: A synthetic approach of stereospecific and racemic S. mosellana pheromones was presented. This method afforded the stereospecific and racemic S. mosellana pheromones in three steps and high enantioselectivity (> 98% ee for (2S,7S)-2,7-nonanediyl dibutyrate) in less than 1 day with 74% and 73% overall yields, respectively, whereas most conventional methods require longer synthesis time with less than 40% yield. The synthesis routes could quickly and economically afford the pheromones, starting from synthon (S)-but-3-yn-2-ol (1a) or but-3-yn-2-ol (1b), through the same three-step processes of coupling, reduction, and esterification. The Y-tube olfactometer results showed significant attractiveness of the synthetic stereospecific and racemic sex pheromones to S. mosellana males relative to the blank control (P < 0.001). Field trials also demonstrated significant attractiveness of the synthetic stereospecific and racemic sex pheromones relative to the blank control (P < 0.001).CONCLUSION: This modular approach is conducive to the deployment of field traps and timely responses to S. mosellana outbreaks and can be a time-saving and cost-effective tool to manage S. mosellana.

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Section: Discussionmentioning

confidence: 99%

Modular synthesis of the pheromone (2S,7S)‐2,7‐nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae)

et al. 2022

Pest Management Science

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Synthesis of All the Stereoisomers of 6-Methyl-2-octadecanone, 14-Methyl-2-octadecanone, and 6,14-Dimethyl-2-octadecanone, Sex Pheromone Components of theLyclene dharma dharmaMoth, from the Enantiomers of Citronellal

Shikichi

Mori

2012

Bioscience, Biotechnology, and Biochemistry

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Synthesis of (1R,7Z)-1-Methyl-7-hexadecenyl Acetate, the Female Sex Pheromone of the Honey Locust Gall Midge

Cited by 2 publications

References 9 publications

Modular synthesis of the pheromone (2S,7S)‐2,7‐nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae)

Modular synthesis of the pheromone (2S,7S)‐2,7‐nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae)

Synthesis of All the Stereoisomers of 6-Methyl-2-octadecanone, 14-Methyl-2-octadecanone, and 6,14-Dimethyl-2-octadecanone, Sex Pheromone Components of theLyclene dharma dharmaMoth, from the Enantiomers of Citronellal

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