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Russian Journal of Organic Chemistry

, Volume 55, Issue 6, pp 831–836 | Cite as

Synthetic Approaches to 15-Deoxy-Δ12,14-prostaglandin J2. A New Key Building Block Based on (3aR,6R,6aS)-6-Trimethylsilyl)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one

  • A. M. Gimazetdinov
  • A. Z. Al’mukhametov
  • M. S. MiftakhovEmail author
Review
  • 10 Downloads

Abstract

{(1S,4R,5R)-5-[tert-Butyl(dimethyl)silyloxymethyl]-4-hydroxycyclopent-2-en-1-yl}acetaldehyde, the key building block in a possible approach to 15-deoxy-Δ12,14-prostaglandin J2, has been synthesized starting from (3aR,6R,6aS)-6-(trimethylsilyl)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one.

Keywords

cyclopentenone prostaglandins 15-deoxy-Δ12,14-prostaglandin J2 asymmetric synthesis bicyclic γ-lactone allylsilane 

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Notes

Acknowledgments

The spectral data were obtained using the equipment of the Chemistry Joint Center (Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

This study was performed in the framework of state assignment no. AAAA-A17-117011910032-4 and was financially supported in part by the Russian Foundation for Basic Research (project nos. 17-43-020326-Povolzh’e, 18-53-00 011-Bel_a).

References

  1. 1.
    Straus, D.S. and Glass, C.K., Med. Res. Rev., 2001, vol. 21, p. 185. doi  https://doi.org/10.1002/med.1006 CrossRefGoogle Scholar
  2. 2.
    Shibata, T., Kondo, M., Osawa, T., Shibata, N., Kobayashi, M., and Uchida, K., J. Biol. Chem., 2002, vol. 277, p. 10459. doi  https://doi.org/10.1074/jbc.M110314200 CrossRefGoogle Scholar
  3. 3.
    Egger, J., Fisher, S., Bretscher, P., Freigang, S., Kopf, M., and Carreira, E.M., Org. Lett., 2015, vol. 17, p. 4340. doi  https://doi.org/10.1021/acs.orglett.5b02181 CrossRefGoogle Scholar
  4. 4.
    Brummond, K.M., Sill, P.C., and Chen, H., Org. Lett., 2004, vol. 6, p. 149. doi  https://doi.org/10.1021/ol035590v CrossRefGoogle Scholar
  5. 5.
    Acharya, H.P. and Kobayashi, Y., Tetrahedron Lett., 2004, vol. 45, p. 1199. doi  https://doi.org/10.1016/j.tetlet.2003.11.143 CrossRefGoogle Scholar
  6. 6.
    Acharya, H.P. and Kobayashi, Y., Tetrahedron, 2006, vol. 62, p. 3329. doi  https://doi.org/10.1016/j.tet.2006.01.051 CrossRefGoogle Scholar
  7. 7.
    Yang, A., Ph.D. Thesis, University of Pittsburgh, Pittsburgh, 2007.Google Scholar
  8. 8.
    Bickley, J.F., Jadav, V., Roberts, S.M., Santoro, M.G., Steiner, A., and Sutton, P.W., Synlett, 2003, no. 8, p. 1170. doi  https://doi.org/10.1055/s-2003-39885
  9. 9.
    Kim, E.H. and Surch, Y.J., Biochem. Pharmacol., 2006, vol. 72, p. 1516. doi  https://doi.org/10.1016/j.bcp.2006.07.030 CrossRefGoogle Scholar
  10. 10.
    Vostrikov, N.S., Lobko, I.F., and Miftakhov, M.S., Tetrahedron Lett., 2014, vol. 55, p. 5622. doi  https://doi.org/10.1016/j.tetlet.2014.08.096 CrossRefGoogle Scholar
  11. 11.
    Iqbal, M., Li, Y., and Evans, P., Tetrahedron, 2004, vol. 60, p. 2531. doi  https://doi.org/10.1016/j.tet.2004.01.048 CrossRefGoogle Scholar
  12. 12.
    Brunoldi, E.M., Zanoni, G., Vidari, G., Sasi, S., Freeman, M.L., Milne, G.L., and Morrow, J.D., Chem. Res. Toxicol., 2007, vol. 20, p. 1528. doi  https://doi.org/10.1021/tx700231a CrossRefGoogle Scholar
  13. 13.
    Uchida, K. and Shibata, T., Chem. Res. Toxicol., 2008, vol. 21, p. 138. doi  https://doi.org/10.1021/tx700177j CrossRefGoogle Scholar
  14. 14.
    Pande, V. and Ramos, M.J., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 4057. doi  https://doi.org/10.1016/j.bmcl.2005.06.025 CrossRefGoogle Scholar
  15. 15.
    Gimazetdinov, A.M., Gataullin, S.S., Bushmarinov, I.S., and Miftakhov, M.S., Tetrahedron, 2012, vol. 68, p. 5754. doi  https://doi.org/10.1016/j.tet.2012.05.036 CrossRefGoogle Scholar
  16. 16.
    Gimazetdinov, A.M., Al’mukhametov, A.Z., Spirikhin, L.V., and Miftakhov, M.S., Russ. J. Org. Chem., 2017, vol. 53, p. 821.CrossRefGoogle Scholar
  17. 17.
    Gimazetdinov, A.M., Al’mukhametov, A.Z., Spirikhin, L.V., and Miftakhov, M.S., Tetrahedron Lett., 2017, vol. 58, p. 3242. doi  https://doi.org/10.1016/j.tetlet.2017.07.023 CrossRefGoogle Scholar
  18. 18.
    Yun, S.Y., Zheng, J.-C., and Lee, D., J. Am. Chem. Soc., 2009, vol. 131, p. 8413. doi  https://doi.org/10.1021/ja903526g CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. M. Gimazetdinov
    • 1
  • A. Z. Al’mukhametov
    • 1
  • M. S. Miftakhov
    • 1
    Email author
  1. 1.Ufa Institute of Chemistry, Ufa Federal Research CenterRussian Academy of SciencesUfa, BashkortostanRussia

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