A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids

Scholarly Works

• Gyrdymova, Y. V.; Rumyantcev, R. V.; Esaulkova, Y. L.; Belyaevskaya, S. V.; Zarubaev, V. V.; Kayumov, A. R.; Rubtsova, S. A. New trifluoromethylated sesquiterpenoids: synthesis, rearrangement, and biological activity. New Journal of Chemistry 2022, 46, 23165–23172. doi:10.1039/d2nj04611c
• Le, T. M.; Szakonyi, Z. Enantiomeric Isopulegol as the Chiral Pool in the Total Synthesis of Bioactive Agents. Chemical record (New York, N.Y.) 2021, 22, e202100194. doi:10.1002/tcr.202100194
• Ilyina, I. V.; Patrusheva, O. S.; Zarubaev, V. V.; Misiurina, M. A.; Slita, A. V.; Esaulkova, I. L.; Korchagina, D. V.; Gatilov, Y. V.; Borisevich, S. S.; Volcho, K. P.; Salakhutdinov, N. F. Influenza antiviral activity of F- and OH-containing isopulegol-derived octahydro-2H-chromenes. Bioorganic & medicinal chemistry letters 2020, 31, 127677. doi:10.1016/j.bmcl.2020.127677
• Il'ina, I. V.; Patrusheva, O. S.; Korchagina, D. V.; Volcho, K. P.; Salakhutdinov, N. F. Synthesis of Fluorinated Octahydro-2H-Chromenes in the Presence of the BF3·Et2O–H2O Catalytic System. Chemistry of Heterocyclic Compounds 2020, 56, 867–874. doi:10.1007/s10593-020-02743-z
• Sidorenko, A.; Kravtsova, A.; Aho, A.; Heinmaa, I.; Wärnå, J.; Pazniak, H.; Volcho, K. P.; Salakhutdinov, N. F.; Murzin, D. Y.; Agabekov, V. Highly selective Prins reaction over acid-modified halloysite nanotubes for synthesis of isopulegol-derived 2H-chromene compounds. Journal of Catalysis 2019, 374, 360–377. doi:10.1016/j.jcat.2019.05.009
• Li-Zhulanov, N.; Il'ina, I. V.; Chicca, A.; Schenker, P.; Patrusheva, O. S.; Nazimova, E. V.; Korchagina, D. V.; Krasavin, M.; Volcho, K. P.; Salakhutdinov, N. F. Effect of chiral polyhydrochromenes on cannabinoid system. Medicinal Chemistry Research 2019, 28, 450–464. doi:10.1007/s00044-019-02294-9
• Li-Zhulanov, N. S.; Zakharenko, A. L.; Chepanova, A. A.; Patel, J.; Zafar, A.; Volcho, K. P.; Salakhutdinov, N.; Reynisson, J.; Leung, I. K. H.; Lavrik, O. I. A Novel Class of Tyrosyl-DNA Phosphodiesterase 1 Inhibitors That Contains the Octahydro-2H-chromen-4-ol Scaffold. Molecules (Basel, Switzerland) 2018, 23, 2468. doi:10.3390/molecules23102468
• Patrusheva, O. S.; Volcho, K. P.; Salakhutdinov, N. F. Synthesis of oxygen-containing heterocyclic compounds based on monoterpenoids. Russian Chemical Reviews 2018, 87, 771–796. doi:10.1070/rcr4810
• Ilyina, I. V.; Zarubaev, V. V.; Lavrentieva, I. N.; Shtro, A. A.; Esaulkova, I. L.; Korchagina, D. V.; Borisevich, S. S.; Volcho, K. P.; Salakhutdinov, N. F. Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses. Bioorganic & medicinal chemistry letters 2018, 28, 2061–2067. doi:10.1016/j.bmcl.2018.04.057
• Patrusheva, O. S.; Pavlova, A.; Korchagina, D. V.; Tolstikova, T. G.; Volcho, K. P.; Salakhutdinov, N. F. Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2-Chromen-4,8-Diols Containing Alkyl-Substituted Aromatic Moieties. Chemistry of Natural Compounds 2017, 53, 1066–1071. doi:10.1007/s10600-017-2202-1
• Kononova, A. A.; Sokolova, A. S.; Cheresiz, S. V.; Yarovaya, O. I.; Nikitina, R. A.; Chepurnov, A. A.; Pokrovsky, A. G.; Salakhutdinov, N. F. N-Heterocyclic borneol derivatives as inhibitors of Marburg virus glycoprotein-mediated VSIV pseudotype entry. MedChemComm 2017, 8, 2233–2237. doi:10.1039/c7md00424a
• Patrusheva, O. S.; Zarubaev, V. V.; Shtro, A. A.; Orshanskaya, Y. R.; Boldyrev, S. A.; Ilyina, I. V.; Kurbakova, S. Y.; Korchagina, D. V.; Volcho, K. P.; Salakhutdinov, N. F. Anti-influenza activity of monoterpene-derived substituted hexahydro-2H-chromenes. Bioorganic & medicinal chemistry 2016, 24, 5158–5161. doi:10.1016/j.bmc.2016.08.037

Explore citations to this article at