Abstract
A synthetic approach is described for the transformation of R-(-)-carvone to methyl (2Z,5S,6E)-5-[(tert-butoxycarbonyl)amino]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate, the key building block for the convergent synthesis of the known antitumor macrolactam ixabepilone. The synthetic sequence includes 10 stages, where the key stage is Curtius rearrangement. Optimal conditions have been found for that rearrangement.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Altmann, K.-H., Pfeiffer, B., Arsenjiyadis, S., Pratt, B.A., and Nicolaou, K.C., Chem. Med. Chem., 2007, vol. 2, p. 396. doi 10.1002/cmdc.200600206
Cao, Y.-N., Zheng, L.-Li., Wang, D., Liang, X.-X., Gao, F., and Zhou, X.-L., Eur. J. Med. Chem., 2018, vol. 143, p. 806. doi 10.1016/j.ejmech.2017.11.062
Watkins, E.B., Chittiboyina, A.G., and Avery, M.A., Eur. J. Org. Chem., 2006, p. 4071. doi 10.1002/ejoc.200600149
Conlin, A., Fornier, M., Hudis, C., Kar, S., and Kirkpatrick, P., Nat. Rev. Drug Discovery, 2007, vol. 12, p. 953. doi 10.1038/nrd2469
Alihodzic, S., Bukvic, M., Elenkov, I.J., Hutinec, A., Kostrun, S., Pesic, D., Saxty, G., Tomaskovich, L., and Ziher, D., Prog. Med. Chem., 2018, vol. 57, p. 113. doi 10.1016/bs.pmch.2018.01.002
Valeev, R.F., Sunagatullina, G.R., Loza, V.V., and Miftakhov, M.S., Russ. J. Org. Chem., 2018, vol. 54, p. 1548. doi 10.1134/S1070428018100172
Erb, W., Levanen, G., Roisnel, T., and Dorcet, V., New J. Chem., 2018, vol. 42, p. 3808. doi 10.1039/C7NJ05020H
Bose, D.S. and Reddy, A.V.N., Tetrahedron Lett., 2003, vol. 44, 3543. doi 10.1016/S0040-4039(03)00623-3
Bal, B.S., Childers, W.E., and Pinnick, H.W., Tetra-hedron, 1981, vol. 37, p. 2091. doi 10.1016/S0040-4020(01)97963-3
Acknowledgments
The spectral studies and theoretical calculations were carried out using the equipment of the “Chemistry” joint center, Ufa Institute Chemistry (Ufa Federal Research Center, Russian Academy of Sciences).
Funding
Thus study was performed in the framework of state assignment no. AAAA-A17-117011910032-4.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interests.
Additional information
Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 9, pp. 1461–1464.
Rights and permissions
About this article
Cite this article
Valeev, R.F., Sunagatullina, G.R. & Miftakhov, M.S. New Key Building Block for Ixabepilone from R-(-)-Carvone. Russ J Org Chem 55, 1370–1373 (2019). https://doi.org/10.1134/S1070428019090161
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428019090161