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Mendeleev Communications, 2022, Volume 32, Issue 1, Pages 97–99
DOI: https://doi.org/10.1016/j.mencom.2022.01.031 (Mi mendc583) 		 
This article is cited in 5 scientific papers (total in 5 papers)

Communications

19F NMR determination of the C20 absolute configuration of C21-fluorinated arylthevinols

M. V. Zelentsovaa, I. V. Sandulenkoa, E. K. Melnikovaab, S. K. Moiseeva

a A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
b Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
Full-text PDF (392 kB) Citations (5)
DOI: https://doi.org/10.1016/j.mencom.2022.01.031
Abstract: 21,21,21-Trifluoro(aryl)thevinols were synthesized by the reaction of 21,21,21-trifluorothevinone with aryl Grignard reagents. The absolute configuration at C20 atom in these CF3-substituted alcohols can be easily determined by one-dimensional 19F NMR spectroscopy that was verified by X-ray diffraction studies.
Keywords: thevinone, thevinols, orvinols, alkaloids, organofluorine compounds, Grignard reaction, absolute configuration, 19F NMR.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (2.3 Mb)


Citation: M. V. Zelentsova, I. V. Sandulenko, E. K. Melnikova, S. K. Moiseev, “19F NMR determination of the C20 absolute configuration of C21-fluorinated arylthevinols”, Mendeleev Commun., 32:1 (2022), 97–99
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  • https://www.mathnet.ru/eng/mendc/v32/i1/p97
    • This publication is cited in the following 5 articles:
    1. János Marton, Paul Cumming, Kenner C. Rice, Joannes T. M. Linders, “Morphinan Alkaloids and Their Transformations: A Historical Perspective of a Century of Opioid Research in Hungary”, IJMS, 26:6 (2025), 2736  crossref
    2. Irina V. Sandulenko, Ekaterina S. Kovaleva, Maria V. Zelentsova, Asmik A. Ambartsumyan, Sergey N. Gorlov, Anastasia A. Danshina, Rinat R. Aysin, Sergey K. Moiseev, “Control of the diastereoselectivity at C(20) in the formation of C(21)-fluorinated thevinols”, Org. Biomol. Chem., 21:7 (2023), 1440  crossref
    3. Maria V. Zelentsova, Irina V. Sandulenko, Asmik A. Ambartsumyan, Anastasia A. Danshina, Sergey K. Moiseev, “C(21)-Di- and monofluorinated scaffold for thevinol/orvinol-based opioid receptor ligands”, Org. Biomol. Chem., 21:45 (2023), 9091  crossref
    4. Irina V. Sandulenko, Irina V. Belozertseva, Edwin E. Zvartau, Maria V. Zelentsova, Asmik A. Ambartsumyan, Alexander F. Smol'yakov, Sergey K. Moiseev, “C(21)-fluorinated thevinol scaffold for opioid ligands. 21,21,21-Trifluoro-6-O-nororvinols: Design, synthesis and analgesic activity”, European Journal of Medicinal Chemistry, 252 (2023), 115296  crossref
    5. János Marton, Anikó Fekete, Paul Cumming, Sándor Hosztafi, Pál Mikecz, Gjermund Henriksen, “Diels–Alder Adducts of Morphinan-6,8-Dienes and Their Transformations”, Molecules, 27:9 (2022), 2863  crossref
    Citing articles in Google Scholar: Russian citations, English citations
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