Abstract
The synthesis of (±)-5-methylidene-4-oxocyclopent-2-en-1-ylacetic acid ethanolamide from the corresponding methyl ester is described. The key step is the oxidation of (±)-(1S*,5R*)-4-oxo-5-phenylthiomethylcyclopent-2-en-1-ylacetic acid ethanolamide with gem-bis(hydroperoxy)cyclohexane.
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Funding
The work was carried out within the framework of the Russian state assignment No. 122031400261-4.
The spectroscopic part of the work and theoretical calculations were performed using the equipment of the Chemistry Center for Collective Use of the Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences.
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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. 2425–2429, October, 2023.
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Makaev, Z.R., Vostrikov, N.S., Gimazetdinov, A.M. et al. Synthesis of (±)-5-methylidene-4-oxocyclopent-2-en-1-ylacetic acid ethanolamide. Russ Chem Bull 72, 2425–2429 (2023). https://doi.org/10.1007/s11172-023-4043-3
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DOI: https://doi.org/10.1007/s11172-023-4043-3