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Transformation of C4-Methyl Derivatives of Levoglucosenone to 2,5-Dihydrofurans. An Unexpected Intramolecular Oxacyclization

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Abstract

The acid-catalyzed reaction of C4-methyl derivatives of levoglucosenone with ethanethiol and propane-1,3-dithiol was studied. The reaction takes a nontrivial route and involves intramolecular oxacyclization to form 2,5-dihydrofurans containing a thioacetal group at C5 in the side chain. The transformation provides a short way to synthesize chiral 2,5,5-trialkyl-substituted 2,5-dihydrofurans from levoglucosenone.

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References

  1. Kochetkov, N.K., Sviridov, A.F., Ermolenko, M.S., Yashunskii, D.V., and Chizhov, O.S., Uglevody v sinteze prirodnykh coedinenii (Carbohydrates in the Synthesis of Natural Compounds), Moscow: Nauka, 1984.

    Google Scholar 

  2. McIntosh, M.C. and Weinrebs, S.M., J. Org. Chem., 1991, vol 56, p. 5010. https://doi.org/10.1021/jo00017a005

    Article  CAS  Google Scholar 

  3. Ghorai, S., Mukhopadhyay, R., Kundu, A.P., and Bhattacharjya, A., Tetrahedron, 2005, vol. 61, p. 2999. https://doi.org/10.1016/j.tet.2005.01.119

    Article  CAS  Google Scholar 

  4. Krohn, K. and Börner, G., J. Org. Chem., 1994, vol. 59, p. 6063. https://doi.org/10.1021/jo00099a043

    Article  CAS  Google Scholar 

  5. Krohn, K. and Börner, G., J. Org. Chem., 1991, vol. 56, p. 6038. https://doi.org/10.1021/jo00021a015

    Article  CAS  Google Scholar 

  6. McCartney, J.L., Meta, C.T., Cicchillo, R.M., Bernardina, M.D., Wagner, T.R., and Norris, P., J. Org. Chem., 2003, vol. 68, p. 10152. https://doi.org/10.1021/jo0350256

    Article  CAS  Google Scholar 

  7. Bruns, W., Horns, S., and Redlich, H., Synthesis, 1995, p. 335. https://doi.org/10.1055/s-1995-3904

    Google Scholar 

  8. Davydova, A.N., Sharipov, B.T., and Valeev, F.A., Russ. J. Org. Chem., 2015, vol. 51, p. 1408. https://doi.org/10.1134/S1070428015100097

    Article  CAS  Google Scholar 

  9. Krohn, K. and Heins, H., J. Carbohydr. Chem., 1991, vol. 10, p. 917. https://doi.org/10.1080/07328309108543960

    Article  CAS  Google Scholar 

  10. Sharipov, B.T., Davidova, A.N., and Valeev, F.A., Chem. Heterocycl. Comp., 2018, vol. 54, p. 403. https://doi.org/10.1007/s10593-018-2277-z

    Article  CAS  Google Scholar 

  11. Lipshutz, B.H. and Garcia, E., Tetrahedron Lett., 1990, vol. 31, p. 7261. https://doi.org/10.1016/S0040-4039(00)88539-1

    Article  CAS  Google Scholar 

  12. Guenoun, F., Lazaro, R., Negro, A., and Viallefont, P., Tetrahedron Lett., 1990, vol. 31, p. 2153. https://doi.org/10.1016/0040-4039(90)80096-5

    Article  CAS  Google Scholar 

  13. Khandekar, G., Robinson, G.C., Stacey, N.A., Steel, P.G., Thomas, E.J., and Vather, S., J. Chem. Soc., Chem. Commun., 1987, p. 877. https://doi.org/10.1039/C39870000877

    Google Scholar 

  14. Sato, T., Nakakita, M., Kimura, S., and Fujisawa, T., Tetrahedron Lett., 1989, vol. 30, p. 977. https://doi.org/10.1016/S0040-4039(00)95295-X

    Article  CAS  Google Scholar 

  15. Clarke, P.A. and Cridland, A.P., Org. Lett., 2005, vol. 7, p. 4221. https://doi.org/10.1021/ol051633r

    Article  CAS  Google Scholar 

  16. Chakraborti, A.K. and Gulhane, R., Chem. Commun., 2003, p. 1896. https://doi.org/10.1039/b304178f

    Google Scholar 

  17. Misra, A.K., Tiwari, P., and Madhusudan, S.K., Carbohydr. Res., 2005, vol. 340, p. 325. https://doi.org/10.1016/j.carres.2004.11.021

    Article  CAS  Google Scholar 

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Acknowledgments

Analyses were performed using the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Ufa Research Center, Russian Academy of Sciences.

Funding

The work was performed according to the State order (contract no. АААА-А17-117011910022-5) and financially supported by the Russian Foundation for Basic Research (project no. 17-43-020166 r_a).

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Authors and Affiliations

  1. Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, pr. Oktyabrya 69, Ufa, Republic of Bashkortostan, 450054, Russia

    A. N. Davydova, B. T. Sharipov & F. A. Valeev

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  1. A. N. Davydova
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  2. B. T. Sharipov
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  3. F. A. Valeev
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Corresponding author

Correspondence to B. T. Sharipov.

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The authors declare no conflict of interest.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 11, pp. 1680–1688.

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Davydova, A.N., Sharipov, B.T. & Valeev, F.A. Transformation of C4-Methyl Derivatives of Levoglucosenone to 2,5-Dihydrofurans. An Unexpected Intramolecular Oxacyclization. Russ J Org Chem 55, 1661–1668 (2019). https://doi.org/10.1134/S1070428019110034

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