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Insect pheromones and their analogs. XIII. Synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates — Components of the sex pheromones ofGrapholitha funebrana andGrapholitha molesta

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Abstract

A new route is proposed for the synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates which is based on the reaction of the Grignard reagent from the readily accessible 1-bromo-5-(1-ethoxyethoxy)pentane with 1-bromohept-3-yne — the bromide obtained from product of the β-hydroxyethylation of pent-1-yne with 2-chloroethylvinyl ether, hept-3-yn-1-ol, by a double decomposition reaction of its tosylate with lithium bromide. The key synthon — dodec-8-yn-1-ol — was converted with the aid of sodium in liquid ammonia into the stereochemical individual dodec-8E-enol, while its reduction with the aid of 9-borabicyclo[3.3.1]nonane (BBN) gave the steroisomeric alcohol exclusively with the Z configuration, as followed from the results of capillary GLC and the IR spectra of the corresponding acetates. The PMR spectra of the compounds synthesized are also given.

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Authors
  1. V. N. Odinokov
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  2. G. Yu. Ishmuratov
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  3. G. G. Balezina
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  4. G. A. Tolstikov
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Additional information

Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 398–400, May–June, 1985.

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Odinokov, V.N., Ishmuratov, G.Y., Balezina, G.G. et al. Insect pheromones and their analogs. XIII. Synthesis of dodec-8E-enyl and dodec-8Z-enyl acetates — Components of the sex pheromones ofGrapholitha funebrana andGrapholitha molesta . Chem Nat Compd 21, 372–374 (1985). https://doi.org/10.1007/BF00574216

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  • DOI: https://doi.org/10.1007/BF00574216

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