Skip to main content
Log in

Allobetulin Ring A Contraction Effected by Sulfur Diethylaminotrifluoride

  • Letters to the Editor
  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The action of sulfur diethylaminotrifluoride on 19β,28-epoxyoleanan-3-ol (allobetulin) causes dehydration of the terpenoid and isomerization of the ring A via its contraction to isopropylcyclopentene ring resulting in 19β,28-epoxy-A-neo-18α-olean-3(5)-ene (α-allobetulin) in a high yield.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. Dehaen, W., Mashentseva, A.A., and Seitembetov, T.S., Molecules, 2011, vol. 16, p. 2443. doi 10.3390/molecules16032443

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Tolstikov, G.A., Flekhter, O.B., Shults, E.E., Baltina, L.A., and Tolstikov, A.G., Khimiya v interesakh ustoichvogo razvitiya, 2005, vol. 13, p. 1.

    CAS  Google Scholar 

  3. Kazakova, O.B., Smirnova, I.E., Khusnutdinova, E.F., Zhukova, O.S., Fetisova, L.V., Apryshko, G.N., Medvedeva, N.I., Yamansarov, E.Yu., Baikova, I.P., Nguyen, T.T., and Thu, D.T., Russ. J. Bioorg. Chem., 2014, vol. 40, no. 5, p. 558. doi 10.1134/S1068162014050082

    Article  CAS  Google Scholar 

  4. Heller, L., Obernauer, A., and Csuk, R., Bioorg. Med. Chem., 2015, vol. 23, p. 3002. doi 10.1016/j.bmc.2015.05.015

    Article  CAS  PubMed  Google Scholar 

  5. Hiyama, T., Organofluorine Compounds: Chemistry and Applications, Heidelberg: Springer-Verlag, 2000.

    Book  Google Scholar 

  6. Zhou, Y., Wang, J., Gu, Z., Wang, S., Zhu, W., Acena, J.L., Soloshonok, V.A., Izawa, K., and Liu, H., Chem. Rev., 2016, vol. 116, p. 422. doi 10.1021/acs.chemrev.5b00392

    Article  CAS  PubMed  Google Scholar 

  7. Gustafsson, T., Gilmour, R., and Seeberger, P.H., Chem. Commun., 2008, p. 3022. doi 10.1039/b803695k

    Google Scholar 

  8. Baumann, M., Baxendale, I.R., Martin, L.J., and Ley, S.V., Tetrahedron, 2009, vol. 65, p. 6611. doi 10.1016/j.tet.2009.05.083

    Article  CAS  Google Scholar 

  9. Li, T.-S., Wang, J.-X., and Zheng, X.-J., J. Chem. Soc. Perkin Trans. 1, 1998, p. 3957. doi 10.1039/A806735J

    Google Scholar 

  10. Schulze, H. and Pieroh, K., Chem. Ber., 1922, vol. 55, p. 2332. doi 10.1002/cber.19220550814

    Article  Google Scholar 

  11. Dischendorfer, O. and Juvan, H., Monatsh. Chem., 1930, vol. 56, p. 272. doi 10.1007/BF02716061

    Article  CAS  Google Scholar 

  12. Pettit, G.R., Green, B., and Bowyer, W.J., J. Org. Chem., 1961, vol. 26, p. 2879. doi 10.1021/jo01066a061

    Article  CAS  Google Scholar 

  13. Lavoie, S., Pichette, A., Garneau, F.-X., Girard, M., and Gaudet, D., Synth. Commun., 2001, vol. 31, no. 10, p. 1565. doi 10.1081/scc-100104070

    Article  CAS  Google Scholar 

  14. Anjaneyulu, A.S.R., Rao, M.N., Sree, A., and Murty, V.S., Ind. J. Chem. (B), 1980, vol. 19, p. 735.

    Google Scholar 

  15. Ferret, H., Dechamps, I., Pardo, D. G., Van Hijfte, L., and Cossy, J., Arkivoc, 2010, vol. viii, p. 126. doi 10.3998/ark.5550190.0011.812

    Google Scholar 

  16. RU Patent 2184120, 2002; Byull. Izobret., 2002, no. 18.

  17. Flekhter, O.B., Karachurina, L.T., Poroikov, L.R., Nigmatullina, L.R., Baltina, L.A., Zarudii, F.S., Davydova, V.A., Spirikhin, L.V., Baikova, I.P., Galin, F.Z., and Tolstikov, G.A., Russ. J. Bioorg. Chem., 2000, vol. 26, no. 3, p. 192. doi 10.1007/BF02786345

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. G. Trishin.

Additional information

Dedicated to the 110th anniversary of M.I. Kabachnik’s birth

Original Russian Text © A.N. Fedorov, D.E. Samoilenko, M.V. Shafeeva, V.V. Abzianidze, Yu.G. Trishin, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1580–1583.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fedorov, A.N., Samoilenko, D.E., Shafeeva, M.V. et al. Allobetulin Ring A Contraction Effected by Sulfur Diethylaminotrifluoride. Russ J Gen Chem 88, 1948–1950 (2018). https://doi.org/10.1134/S1070363218090347

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218090347

Keywords

Navigation