Abstract
Previously unknown optically active cyclopentenones were synthesized by the ozonation of 2-dichloromethyl-5-(1-methylethylidene)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide in CH2Cl2–MeOH (10 : 1) at 0°C and of (3aR,6aR)-3-hydroxy-6-(1-methylethylidene)-2-[(1R)-1-phenylethyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one in cyclohexane–MeOH (10 : 1) at 5°C until complete consumption of the starting compounds (by TLC), followed by treatment with Me2S. The new obtained cyclopentenons: 2-(dichloromethyl)-5-oxo-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide and (3aR,6aR)-3-hydroxy-2-[(1R)-1-phenylethyl]-2,3,3a,6a-tetrahydrocyclopenta[c]pyrrole-1,6-dione are useful compounds to prepare cyclopentanoids.
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ACKNOWLEDGMENTS
Analyses were performed on the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Russian Academy of Sciences.
Funding
The work was performed under the state order, topic “Design and Synthesis of Bioactive Natural and Non-natural Cyclopentanoides, Heterocycles, Epothilones and Analogs” (no. 122031400261-4).
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Valiullina, Z.R., Ivanova, N.A. & Miftakhov, M.S. Reaction of Derivatives of the [2+2]-Cycloadduct of Dichloroketene and Dimethylfulvene with Ozone. Russ J Org Chem 60, 349–352 (2024). https://doi.org/10.1134/S1070428024020180
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DOI: https://doi.org/10.1134/S1070428024020180