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The absolute configuration of (+)- and (−)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris

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Abstract

Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)-[η6-(3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH4-NiCl2·6H2O reagent system in MeOH leads to (−)-1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives (R)-(−)-acetoxydodecanoic acid, lactonization of which leads to the known (R)-(+)-4-dodecanolide. The starting (+)-1-phenylundec-4-yn-3-ol was thus shown to have the S-configuration.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. L. Vlasyuk, G. D. Gamalevich & E. P. Serebryakov

  2. Department of Chemistry, M. V. Lomonosov Moscow State University, Str. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    V. A. Voblikova

Authors
  1. A. L. Vlasyuk
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  2. V. A. Voblikova
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  3. G. D. Gamalevich
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  4. E. P. Serebryakov
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Correspondence to A. L. Vlasyuk.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2032–2036, September, 2013.

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Vlasyuk, A.L., Voblikova, V.A., Gamalevich, G.D. et al. The absolute configuration of (+)- and (−)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris . Russ Chem Bull 62, 2032–2036 (2013). https://doi.org/10.1007/s11172-013-0294-8

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  • DOI: https://doi.org/10.1007/s11172-013-0294-8

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