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Vicinally substituted cyclopentenes and cyclopentenones from (±)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

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Abstract

Solvolysis of (±)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one in a mixture of tert-butyl alcohol with water and triethylamine, followed by successive treatment with K2CO3, NaBH4, and CH2N2, gave methyl 2-(hydroxymethyl)cyclopent-2-ene-1-carboxylate which was subjected to hydride reduction, epoxidation, trichloroacetimidation, and acetylation. Allylic oxidation of methyl 2-(acetoxymethyl)cyclopent-2-ene-1-carboxylate with the chromium(VI) oxide-3,5-dimethylpyrazole complex afforded methyl 2-(acetoxymethyl)-4-oxocyclopent-2-ene-1-carboxylate, and methyl (1R*,2R*,5R*)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]-hexane-2-carboxylate was converted into a building block for the synthesis of deoxyentecavir and sarcomycine methyl ester.

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References

  1. Das, S., Chandrasekhar, S., Singh, Y.J., and Jree, R., Chem. Rev., 2007, vol. 107, p. 3286.

    Article  CAS  Google Scholar 

  2. Bericibar, A., Jrandjean, C., and Sirivardena, A., Chem. Rev., 1999, vol. 99, p. 779.

    Article  Google Scholar 

  3. Erust, M. and Helmchen, J., Angew. Chem., Int. Ed., 2002, vol. 41, p. 4054.

    Article  Google Scholar 

  4. Li, S.W. and Batey, R.A., Chem. Commun., 2007, p. 375.

    Google Scholar 

  5. Toney, J. and Prinet, J., Org. Lett., 2008, vol. 10, p. 45.

    Article  Google Scholar 

  6. Wu, Y. and Jao, J., Org. Lett., 2008, vol. 10, p. 1533.

    Article  CAS  Google Scholar 

  7. Liu, X., Jiao, X., Wu, Q., Tian, C., Li, R., and Xie, P., Tetrahedron Lett., 2012, vol. 53, p. 3805.

    Article  CAS  Google Scholar 

  8. Martinez, A.G., Vilar, E.T., Fraile, A.G., Cerero, S.M., Osuna, S.O., and Maroto, B.L., Tetrahedron Lett., 2001, vol. 42, p. 779.

    Google Scholar 

  9. Gimazetdinov, A.M., Vostrikov, N.S., and Miftahov, M.S., Tetrahedron: Asymmetry, 2008, vol. 19, p. 1094.

    Article  CAS  Google Scholar 

  10. Brady, W.T., Tetrahedron, 1981, vol. 37, p. 2949.

    Article  CAS  Google Scholar 

  11. Gimazetdinov, A.M. and Miftakhov, M.S., Russ. J. Org. Chem., 2009, vol. 45, p. 694.

    Article  Google Scholar 

  12. Corey, E.J. and Fleet, S.W., Tetrahedron Lett., 1973, vol. 14, p. 4499.

    Article  Google Scholar 

  13. Lee, K. and Cha, J.K., J. Am. Chem. Soc., 2001, vol. 123, p. 5590.

    Article  CAS  Google Scholar 

  14. Martin-Rodrigues, M., Jalan-Fernandes, R., Markos-Esribano, A., and Bermeo, F.A., J. Org. Chem., 2009, vol. 74, p. 1798.

    Article  Google Scholar 

  15. Wender, P.A., Rice, K.D., and Schante, M.E., J. Am. Chem. Soc., 1997, vol. 119, p. 7897.

    Article  CAS  Google Scholar 

  16. Nakamura, A. and Nakada, M., Synthesis, 2013, vol. 45, no. 11, p. 1421.

    Article  CAS  Google Scholar 

  17. Kirchner, J.G., Thin-Layer Chromatography, Perry, E.S., Ed., New York: Wiley, 1978, 2nd ed. Translated under the title Tonkosloinaya khromatografiya, Moscow: Mir, 1981, vol. 1, p. 228.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    V. A. Akhmet’yanova, N. A. Ivanova, Z. R. Valiullina & M. S. Miftakhov

Authors
  1. V. A. Akhmet’yanova
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  2. N. A. Ivanova
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  3. Z. R. Valiullina
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  4. M. S. Miftakhov
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Corresponding author

Correspondence to V. A. Akhmet’yanova.

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Original Russian Text © V.A. Akhmet’yanova, N.A. Ivanova, Z.R. Valiullina, M.S. Miftakhov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 3, pp. 337–342.

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Akhmet’yanova, V.A., Ivanova, N.A., Valiullina, Z.R. et al. Vicinally substituted cyclopentenes and cyclopentenones from (±)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one. Russ J Org Chem 51, 319–324 (2015). https://doi.org/10.1134/S1070428015030057

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  • DOI: https://doi.org/10.1134/S1070428015030057

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