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Regiocontrolled cleavage of the isocembrol cycle at the Δ2 bond and its transformation into 15-membered macrolide

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Abstract

Isocembrol C(3)-ketoxime was synthesized regioselectively and the C—C bond was cleaved under the standard Beckmann fragmentation conditions. Subsequent hydrolysis of nitrile to give ω-hydroxy acid and cyclization on treatment with 2,2′-dipyridyl disulfide finalized the synthesis of 15-membered macrolide.

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Acknowledgements

NMR spectra were recorded using the spectrometers of the Center for Collective Use “Khimiya” at the Ufa Institute of Chemistry of the Russian Academy of Sciences and the Regional Ccenter for Collective Use of Unique Equipment “Agidel” at the Ufa Federal Research Center of the Russian Academy of Sciences.

Funding

This work was performed in the framework of the State Tacks (Nos. 123011300044-5 and 122031400259-1).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

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

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

Correspondence to Sh. M. Salikhov.

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No human or animal subjects were used in this research.

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The authors declare no competing interests.

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Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2466–2472, October, 2023.

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Salikhov, S.M., Faizullina, L.K. & Valeev, F.A. Regiocontrolled cleavage of the isocembrol cycle at the Δ2 bond and its transformation into 15-membered macrolide. Russ Chem Bull 72, 2466–2472 (2023). https://doi.org/10.1007/s11172-023-4048-y

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  • DOI: https://doi.org/10.1007/s11172-023-4048-y

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