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Eleuthesides and their analogs: V. Medium- and large-ring lactones based on levoglucosenone

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Abstract

Ozonolysis of the bridging double bond in bicyclic enol ethers obtained by the Michael reaction and subsequent intramolecular etherification afforded chiral decanolides fused to a tetrahydropyran ring. Three-step procedures were developed for the synthesis of chiral lactones with medium and large rings via oxidative cleavage with pyridinium chlorochromate of mixed bicyclic ketals which were prepared by treatment with methanolic HCl of Michael adducts derived from levoglucosenone and cyclopenta-, cyclohexa-, cyclohepta-, and cyclododecanone.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    Yu. A. Khalilova, L. V. Spirikhin, Sh. M. Salikhov & F. A. Valeev

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  1. Yu. A. Khalilova
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  2. L. V. Spirikhin
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  3. Sh. M. Salikhov
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  4. F. A. Valeev
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Correspondence to Yu. A. Khalilova.

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Original Russian Text © Yu.A. Khalilova, L.V. Spirikhin, Sh.M. Salikhov, F.A. Valeev, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 125–135.

For communication IV, see [1].

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Khalilova, Y.A., Spirikhin, L.V., Salikhov, S.M. et al. Eleuthesides and their analogs: V. Medium- and large-ring lactones based on levoglucosenone. Russ J Org Chem 50, 117–127 (2014). https://doi.org/10.1134/S1070428014010229

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  • DOI: https://doi.org/10.1134/S1070428014010229

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