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Reverse ketal-acetal rearrangement of levoglucosenone and cyclohexanone Michael adducts and the possibilities of its use in the synthesis of native topology lactones

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Chemistry of Heterocyclic Compounds Aims and scope

Heating of solutions of the internal hemiketal, obtained by opening the 1,6-anhydro bridge in the Michael adduct of levoglucosenone and cyclohexanone, under reflux in THF or diglyme in the presence of NaH or Na, respectively, leads to the reduction of the hemiketal group to the ether group and oxidation of its alcohol component to the hemiacetal group. The conditions for the reverse transformation were established. Some transformations of the obtained cyclic hemiacetal have been studied. Direct methylation attempts with MeMgI in order to introduce a substituent into the 1,6-anhydro bridge were unsuccessful; therefore, the introduction of the methyl group was carried out after the oxidation of hemiacetal group to the lactone.

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The work was carried out according to the topics No. АААА-А17-117011910022-5, No. АААА-А17-117011910027-0 of the State Assignment and financial support of the Russian Foundation for Basic Research (grant 17-43-020166-р_а).

NMR spectra were recorded on the equipment of the Center for Collective Use of scientific equipment “Chemistry” of Ufa Institute of Chemistry of the Russian Academy of Sciences.

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  1. Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa, 450054, Russia

    Liliya Kh. Faizullina, Yuliya А. Khalilova, Shamil M. Salikhov & Farid A. Valeev

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  1. Liliya Kh. Faizullina
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  2. Yuliya А. Khalilova
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  3. Shamil M. Salikhov
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  4. Farid A. Valeev
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Correspondence to Liliya Kh. Faizullina.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 612–618

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Faizullina, L.K., Khalilova, Y.А., Salikhov, S.M. et al. Reverse ketal-acetal rearrangement of levoglucosenone and cyclohexanone Michael adducts and the possibilities of its use in the synthesis of native topology lactones. Chem Heterocycl Comp 55, 612–618 (2019). https://doi.org/10.1007/s10593-019-02506-5

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  • DOI: https://doi.org/10.1007/s10593-019-02506-5

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