Among nine alicyclic 1,5,9-triketones with differently fused 5-, 6-, and 7-membered rings in the molecule, existing as mixtures of 3–6 diastereomers, only those containing at least two 6-membered rings were capable of intramolecular cyclization in acidic medium (HCl, EtOH). The diastereomer mixture underwent stereoselective transformation, giving one major cyclization product. The relative configuration of chiral centers in cyclization products obtained under acidic or basic conditions was compared by X-ray crystallography. The differences were caused by divergent stereochemical outcome at the first stage of cyclization.
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Notes
The numbers in parentheses indicate the ring size in triketone or diketone.
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The authors gratefully acknowledge the assistance from the Laboratory of Molecular analysis, School of Natural Sciences, Far Eastern Federal University, in performing elemental analyses.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(11), 1079–1085
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Akimova, T.I., Soldatkina, O.A., Gerasimenko, A.V. et al. Reactivity of alicyclic 1,5,9-triketones toward five-, six-, and seven-membered rings in acidic medium. Stereochemistry of intramolecular cyclization products. Chem Heterocycl Comp 57, 1079–1085 (2021). https://doi.org/10.1007/s10593-021-03028-9
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DOI: https://doi.org/10.1007/s10593-021-03028-9