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.
References
Dehaen, W., Mashentseva, A.A., and Seitembetov, T.S., Molecules, 2011, vol. 16, p. 2443. doi 10.3390/molecules16032443
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.
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
Heller, L., Obernauer, A., and Csuk, R., Bioorg. Med. Chem., 2015, vol. 23, p. 3002. doi 10.1016/j.bmc.2015.05.015
Hiyama, T., Organofluorine Compounds: Chemistry and Applications, Heidelberg: Springer-Verlag, 2000.
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
Gustafsson, T., Gilmour, R., and Seeberger, P.H., Chem. Commun., 2008, p. 3022. doi 10.1039/b803695k
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
Li, T.-S., Wang, J.-X., and Zheng, X.-J., J. Chem. Soc. Perkin Trans. 1, 1998, p. 3957. doi 10.1039/A806735J
Schulze, H. and Pieroh, K., Chem. Ber., 1922, vol. 55, p. 2332. doi 10.1002/cber.19220550814
Dischendorfer, O. and Juvan, H., Monatsh. Chem., 1930, vol. 56, p. 272. doi 10.1007/BF02716061
Pettit, G.R., Green, B., and Bowyer, W.J., J. Org. Chem., 1961, vol. 26, p. 2879. doi 10.1021/jo01066a061
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
Anjaneyulu, A.S.R., Rao, M.N., Sree, A., and Murty, V.S., Ind. J. Chem. (B), 1980, vol. 19, p. 735.
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
RU Patent 2184120, 2002; Byull. Izobret., 2002, no. 18.
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
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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.
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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
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DOI: https://doi.org/10.1134/S1070363218090347