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The Facial and Short Method for the Synthesis of Z/E-Isomers of Acetate of 12-Tetradecene-1-ol Components of the Sex Pheromone Ostrinia furnacalis

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The sex pheromones of Ostrinia furnacalis Z/E-isomers of acetate of 12-tetradecene-1-ol were synthesized in an overall yield of 44.5% with 1,12-dodecanediol as a starting material via mono-esterification, PCC oxidation, and the Wittig reaction. The Z/E-isomers ratio was 72:28. Configuration transformation of Z/E-isomers 72:28 mixture treated with sodium nitrite and nitric acid resulted in the production of a mixture with Z/E-isomers 54:46. The products were confirmed by IR, 1H, and 13C NMR spectral data.

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Acknowledgment

This work was financially supported by the Open Fund of Inner Mongolia Industrial Engineering Research Center of Universities for Castor (MDK2016001), National Foundation Cultivation Project of Inner Mongolia University for Nationalities (NMDGP1503). The second batch of industry–university cooperation collaborative education projects of the Ministry of Education in 2019 (201902195001), Opening Project of Key Laboratory of Natural Product Chemistry and Functional Molecular Synthesis Autonomous Region of Inner Mongolia University for Nationalities (MDK2017051).

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Authors and Affiliations

  1. College of Chemistry and Materials, Inner Mongolia University for Nationalities, 028000, Tongliao, P. R. China

    Jiu-ming Li, Ting-ting Huang, Ning Xu, **ng-yang Xu & Hong-cui Yu

  2. Inner Mongolia Industrial Engineering Research Center of Universities for Castor, 028000, Tongliao, P. R. China

    Jiu-ming Li

  3. Inner Mongolia Key Laboratory for the Natural Products Chemistry and Functional Molecular Synthesis, 028000, Tongliao, P. R. China

    Jiu-ming Li

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  1. Jiu-ming Li
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  2. Ting-ting Huang
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  3. Ning Xu
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  4. **ng-yang Xu
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  5. Hong-cui Yu
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Correspondence to Jiu-ming Li.

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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2022, pp. 442–444.

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Li, Jm., Huang, Tt., Xu, N. et al. The Facial and Short Method for the Synthesis of Z/E-Isomers of Acetate of 12-Tetradecene-1-ol Components of the Sex Pheromone Ostrinia furnacalis. Chem Nat Compd 58, 520–523 (2022). https://doi.org/10.1007/s10600-022-03724-8

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  • DOI: https://doi.org/10.1007/s10600-022-03724-8

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