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Synthesis of Nonano-9-lactone Fused to a δ-Lactone Ring

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Abstract

With the goal of obtaining fused dilactones, the carbohydrate moiety of diastereoisomeric Michael adducts of levoglucosenone and cyclohexanone was converted to δ-lactone and its derivatives fused to an octahydrochromene fragment. The subsequent oxidative cleavage of the C-C bridge in the latter by the action of pyridiniun chlorochromate (PCC) afforded nonano-9-lactone fused at the C6-C7 bond to δ-lactone or methyl-δ-lactol. The presence of a carbonyl group in the carbohydrate moiety was found to prevent C-C bond cleavage.

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Acknowledgments

The spectral and analytical data were obtained using the equipment of the Chemistry joint center, Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

This study was performed in the framework of state assignment no. AAAA-A17-117011910022-5 and under financial support by the Russian Foundation for Basic Research (project no. 17-43-020166-r_a).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, 450054, Russia

    L. Kh. Faizullina, A. R. Tagirov, Sh. M. Salikhov & F. A. Valeev

Authors
  1. L. Kh. Faizullina
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  2. A. R. Tagirov
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  3. Sh. M. Salikhov
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  4. F. A. Valeev
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Corresponding author

Correspondence to L. Kh. Faizullina.

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Conflict of Interests

The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1834–1842.

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Faizullina, L.K., Tagirov, A.R., Salikhov, S.M. et al. Synthesis of Nonano-9-lactone Fused to a δ-Lactone Ring. Russ J Org Chem 55, 1832–1839 (2019). https://doi.org/10.1134/S1070428019120042

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  • DOI: https://doi.org/10.1134/S1070428019120042

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