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Synthesis of isomeric 1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonanes and 1’-hydroxybrevicomin from ethyl 5-oxohexenoate ethyleneacetal through cyclopropanation of an ester group followed by oxidative opening of the three-membered ring

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Abstract

Syntheses were performed of (±)-endo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane and (±)-1’-hydroxy-exo-brevicomin constituting racemic forms of the secretion components of pine weever (Hylobius abietis) and bark beetle of upland pines (Dendroctonus ponderosae) through cyclopropanation of the ester group of an available ethyl 5-oxohexanoate ethyleneacetal with the subsequent oxidative opening of the three-membered ring in the compound obtained.

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Authors and Affiliations

  1. Belarussian State University, Minsk, 220030, Belarus

    D. A. Astashko, O. G. Kulinkovich & V. I. Tyvorskii

Authors
  1. D. A. Astashko
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  2. O. G. Kulinkovich
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  3. V. I. Tyvorskii
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Additional information

Original Russian Text © D.A. Astashko, O.G. Kulinkovich, V.I. Tyvorskii, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 5, pp. 736–740.

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Astashko, D.A., Kulinkovich, O.G. & Tyvorskii, V.I. Synthesis of isomeric 1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonanes and 1’-hydroxybrevicomin from ethyl 5-oxohexenoate ethyleneacetal through cyclopropanation of an ester group followed by oxidative opening of the three-membered ring. Russ J Org Chem 42, 719–723 (2006). https://doi.org/10.1134/S1070428006050125

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  • DOI: https://doi.org/10.1134/S1070428006050125

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