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Synthesis of 2,5-dialkyl-substituted tetrahydrofurans — symmetrical analogs of natural acetogenins

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Abstract

An efficient method has been developed for the synthesis of 2,5-dialkyl-substituted tetrahydrofurans, analogues of natural acetogenins. A series of tetrahydrofurans of this type have been obtained using the Ti-catalyzed homo-cyclomagnesiation of terminal 1,2-dienes at the key stage. By Ru-catalyzed oxidation of symmetrical nZ,(n+4)Z—dienes, ketols containing a tetrahydrofuran fragment were synthesized. Diastereoselective reduction of the carbonyl group of these ketols with L-selectride leads to diols, whereas oxidation of their hydroxyl groups with the Dess—Martin periodinane results in the formation of previously unreported diketones in quantitative yields.

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References

  1. A. R. Díaz-Marrero, A. López-Arencibia, C. J. Bethencout-Estrella, F. Cen-Pacheco, I. Sifaoui, A. Hernández Creus, M. C. Duque-Ramárez, M. L. Souto, A. Hernández Daranas, J. Lorenzo-Morales, J. E. Piñero, J. J. Fernández, Bioorg. Chem., 2019, 103276; DOI: https://doi.org/10.1016/j.bioorg.2019.103276.

  2. J. J. Fernández, M. L. Souto, M. Norte, Nat. Prod. Rep., 2000, 17, 235–246; DOI: https://doi.org/10.1039/a909496b.

    Article  PubMed  Google Scholar 

  3. D. A. Kevin II, D. A. Meujo, M. T. Hamann, Expert Opin. Drug Discov., 2009, 4, 109–146; DOI: https://doi.org/10.1517/17460440802661443.

    Article  PubMed  Google Scholar 

  4. L. J. Brown, I. B. Spurr, S. C. Kemp, N. P. Camp, K. R. Gibson, R. C. D. Brown, Org. Lett., 2008, 10, 2489–2492; DOI: https://doi.org/10.1021/ol800767e.

    Article  CAS  PubMed  Google Scholar 

  5. L. Fernández-Peña, C. Diez-Poza, P. González-Andres, A. Barbero, Mar. Drugs, 2022, 20, 120; DOI: https://doi.org/10.3390/md20020120.

    Article  PubMed  PubMed Central  Google Scholar 

  6. A. Bermejo, B. Figadere, M.-C. Zafra-Polo, I. Barrachina, E. Estornell, D. Cortes, Nat. Prod. Rep., 2005, 22, 269; DOI: https://doi.org/10.1039/B500186M.

    Article  CAS  PubMed  Google Scholar 

  7. M. Murai, N. Ichimaru, M. Abe, T. Nishioka, H. Miyoshi, Tetrahedron, 2006, 45, 9778–9787; DOI: https://doi.org/10.1021/bi060713f.

    CAS  Google Scholar 

  8. J. Defretin, C. Gleye, D. Cortes, X. Franck, R. Hocquemiller, B. Figadere, Lett. Org. Chem., 2004, 1, 316–322; DOI: https://doi.org/10.2174/1570178043400460.

    Article  CAS  Google Scholar 

  9. E. Nakamaru-Ogiso, H. Han, A. Matsuno-Yagi, E. Keinan, S. C. Sinha, T. Yagi, T. Ohnishi, FEBS Lett., 2010, 584, 883–888; DOI: https://doi.org/10.1016/j.febslet.2010.01.004.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. N. Kojima, T. Fushimi, N. Maezaki, T. Tanaka, T. Yamori, Bioorg. Med. Chem. Lett., 2008, 18, 1637–1641; DOI: https://doi.org/10.1016/j.bmcl.2008.01.057.

    Article  CAS  PubMed  Google Scholar 

  11. M. Carda, J. Murga, J. Panos, C. A. Angulo-Pachon, J. Garcia-Pla, S. Diaz-Oltra, J. A. Marco, C. Trigili, M. Redondo-Horcajo, J. F. Diaz, I. Barasoain, Curr. Med. Chem., 2013, 20, 1173–1182; DOI: https://doi.org/10.2174/0929867311320090006.

    Article  CAS  PubMed  Google Scholar 

  12. V. A. D’yakonov, A. A. Makarov, A. G. Ibragimov, L. M. Khalilov, U. M. Dzhemilev, Tetrahedron, 2008, 64, 10188–10194; DOI: https://doi.org/10.1016/j.tet.2008.08.041.

    Article  Google Scholar 

  13. V. A. D’yakonov, A. A. Makarov, E. Kh. Makarova, L. M. Khalilov, U. M. Dzhemilev, Russ. J. Org. Chem., 2012, 48, 349–353; DOI: https://doi.org/10.1134/S1070428012030025.

    Article  Google Scholar 

  14. V. A. D’yakonov, A. A. Makarov, E. Kh. Makarova, U. M. Dzhemilev, Tetrahedron, 2013, 69, 8516–8526; DOI: https://doi.org/10.1016/j.tet.2013.06.106.

    Article  Google Scholar 

  15. V. A. D’yakonov, A. A. Makarov, E. Kh. Makarova, L. M. Khalilov, U. M. Dzhemilev, Russ. Chem. Bull., 2012, 61, 1943–1949; DOI: https://doi.org/10.1007/s11172-012-0269-1.

    Article  Google Scholar 

  16. U. M. Dzhemilev, L. I. Khusainova, K. S. Ryazanov, L. O. Khafizova, Russ. Chem. Bull., 2021, 70, 1851–1892; DOI: https://doi.org/10.1007/s11172-021-3292-2.

    Article  CAS  Google Scholar 

  17. V. A. D’yakonov, A. A. Makarov, E. N. Andreev, L. U. Dzhemileva, E. Kh. Makarova, U. M. Dzhemilev, Russ. Chem. Bull., 2020, 69, 386–389; DOI: https://doi.org/10.1007/s11172-020-2772-0.

    Article  Google Scholar 

  18. U. M. Dzhemilev, L. U. Dzhemileva, V. A. D’yakonov, Russ. Chem. Bull., 2023, 72, 404.

    Article  Google Scholar 

  19. M. de Champdor, M. Lasalvia, V. Piccialli, Tetrahedron Lett., 1998, 39, 9781–9784; DOI: https://doi.org/10.1016/S0040-4039(98)02172-8.

    Article  Google Scholar 

  20. T. J. Donohoe, J. G. J. Winter, M. Helliwell, G. Stemp, Tetrahedron Lett., 2001, 42, 971–974; DOI: https://doi.org/10.1016/S0040-4039(00)02225-5.

    Article  CAS  Google Scholar 

  21. T. J. Donohoe, S. Butterworth, Angew. Chem., 2003, 115, 978–981; DOI: https://doi.org/10.1002/ange.200390222.

    Article  Google Scholar 

  22. M. A. Topchiy, A. A. Ageshina, S. A. Rzhevskiy, L. I. Minaeva, M. S. Nechaev, A. F. Asachenko, Russ. Chem. Bull., 2022, 71, 940–945; DOI: https://doi.org/10.1007/s11172-022-3494-2.

    Article  CAS  Google Scholar 

  23. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, V. M. Men’shov, N. E. Nifantiev, Russ. Chem. Bull., 2021, 70, 1356–1362; DOI: https://doi.org/10.1007/s11172-021-3223-2.

    Article  CAS  Google Scholar 

  24. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem., 1981, 46, 3936–3938; DOI: https://doi.org/10.1021/jo00332a045.

    Article  CAS  Google Scholar 

  25. L. Albarella, D. Musu-meci, D. Sica, Eur. J. Org. Chem., 2001, 997–1003; DOI: https://doi.org/10.1002/1099-0690(200103)2001:5<997::AID-EJOC997>3.0.CO;2-7.

  26. V. Piccialli, N. Cavallo, Tetrahedron Lett., 2001, 42, 4695–4699; DOI: https://doi.org/10.1016/S0040-4039(01)00790-0.

    Article  CAS  Google Scholar 

  27. G. Bifulco, T. Caserta, L. Gomez-Paloma, V. Piccialli, Tetrahedron Lett., 2003, 44, 5499–5503; DOI: https://doi.org/10.1016/S0040-4039(03)01254-1.

    Article  CAS  Google Scholar 

  28. T. Caserta, V. Piccialli, L. Gomez-Paloma, G. Bifulco, Tetrahedron, 2005, 61, 927–939; DOI: https://doi.org/10.1016/j.tet.2004.11.018.

    Article  CAS  Google Scholar 

  29. S. Göhler, S. Roth, H. Cheng, H. Göksel, A. Rupp, L. O. Haustedt, C. B. W. Stark, Synthesis, 2007, 17, 2751–2754; DOI: https://doi.org/10.1055/s-2007-983797.

    Google Scholar 

  30. H. Jang, I. Shin, D. Lee, H. Kim, D. Kim, Angew. Chem., Int. Ed., 2016, 55, 6497–6501; DOI:https://doi.org/10.1002/anie.201600637.

    Article  CAS  Google Scholar 

  31. L. Brandsma, Best Synthetic Methods: Acetylenes, Allenes and Cumulenes, Academic Press, New York, 2003, 502 pp.

    Google Scholar 

  32. J. Li, W. Yan, Y. Kishi, J. Am. Chem. Soc., 2015, 137, 6226–6231; DOI: https://doi.org/10.1021/jacs.5b03499.

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    A. A. Makarov, I. V. Ishbulatov & E. Kh. Makarova

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    U. M. Dzhemilev & V. A. D’yakonov

Authors
  1. A. A. Makarov
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  2. I. V. Ishbulatov
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  3. E. Kh. Makarova
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  4. U. M. Dzhemilev
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  5. V. A. D’yakonov
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Correspondence to A. A. Makarov.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

This work was performed under financial support of the Russian Science Foundation (Project No. 22-73-10164).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 3, pp. 689–696, March, 2023.

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Makarov, A.A., Ishbulatov, I.V., Makarova, E.K. et al. Synthesis of 2,5-dialkyl-substituted tetrahydrofurans — symmetrical analogs of natural acetogenins. Russ Chem Bull 72, 689–696 (2023). https://doi.org/10.1007/s11172-023-3833-6

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  • DOI: https://doi.org/10.1007/s11172-023-3833-6

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