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Michael Adducts of Levoglucosenone with α-Ethoxycarbonyl- and α-Nitrocyclododecanones: Transformation into Chiral Macrolides

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Chemistry of Heterocyclic Compounds Aims and scope

Levoglucosenone reacted with α-ethoxycarbonyl- and α-nitrocyclododecanones, leading to the formation of diastereomeric Michael adducts in high yields. Methods were developed for the denitration of the respective nitroadducts by treatment with Raney nickel and Bu3SnH, allowing to optimize the synthesis of a 16-membered chiral macrolide.

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Notes

  1. Here and further in the Experimental part square parentheses are used to indicate the different chemical signals of minor diastereomers. The exooriented hydrogen atoms of levoglucosenone system are denoted as НA and the endo-oriented hydrogen atoms are denoted as НВ, while for the rest of the СН2 groups the assignment was not made

  2. In the cases where the signals of both diastereomers coincide, the overall number of protons is indicated in the parentheses.

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Authors and Affiliations

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

    Liliya Kh. Faizullina, Yulia S. Galimova, Shamil M. Salikhov & Farid A. Valeev

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  1. Liliya Kh. Faizullina
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  2. Yulia S. Galimova
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  3. Shamil M. Salikhov
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  4. Farid A. Valeev
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Correspondence to Farid A. Valeev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(11), 1434–1439

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Faizullina, L.K., Galimova, Y.S., Salikhov, S.M. et al. Michael Adducts of Levoglucosenone with α-Ethoxycarbonyl- and α-Nitrocyclododecanones: Transformation into Chiral Macrolides. Chem Heterocycl Comp 56, 1434–1439 (2020). https://doi.org/10.1007/s10593-020-02834-x

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  • DOI: https://doi.org/10.1007/s10593-020-02834-x

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