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General approach to synthesis of chiral branched hydrocarbons in high configurational purity

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Abstract

Configurationally pure (>99.6%) α-methylalkanoic acids have been employed to prepare chiral hydrocarbon semiochemicals. The stereoisomers of the following compounds were synthesized: 13-methylhentriacontane, 15-methyltritriacontane, and 15,19-dimethyltritriacontane. The first compound was identified earlier as a kairomone of the corn earworm while the other two are sex excitants of the stable fly. The methods described have broad applicability in asymmetric synthesis.

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Authors and Affiliations

  1. U.S. Department of Agriculture, Insect Attractants, Behavior, and Basic Biology Research Laboratory, Agricultural Research Service, 32604, Gainesville, Florida

    Philip E. Sonnet

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  1. Philip E. Sonnet
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Sonnet, P.E. General approach to synthesis of chiral branched hydrocarbons in high configurational purity. J Chem Ecol 10, 771–781 (1984). https://doi.org/10.1007/BF00988542

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  • DOI: https://doi.org/10.1007/BF00988542

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