Skip to main content
SpringerLink
Log in

Synthesis of a New 10,11-Didehydro Analog of Epothilone D

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A new chiral 10,11-didehydro analog of epothilone D with isosteric substitution in the C15–C3 fragment of natural epothilones has been synthesized.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Kingston, D.G.I., Chem. Biol., 2004, vol. 11, p. 153. https://doi.org/10.1016/j.chembiol.2004.02.009

    Article  CAS  PubMed  Google Scholar 

  2. Feyen, F., Cachoux, F., Gertsch, J., Wartmann, M., and Altmann, K.-H., Acc. Chem. Res. 2008, vol. 41, p. 21. https://doi.org/10.1021/ar700157x

  3. Harris, C.R. and Danishefsky, S.J., J. Org. Chem., 1999, vol. 64, p. 8434. https://doi.org/10.1021/jo991006d

    Article  CAS  Google Scholar 

  4. Monti, C., Sharon, O., and Gennari, C., Chem. Commun., 2007, p. 4271. https://doi.org/10.1039/B708820E

  5. Gerth, K., Bedorf, N., Höfle, G., Irshik, H., and Reichenbach, H., J. Antibiot., 1996, vol. 49, p. 560. https://doi.org/10.7164/antibiotics.49.560

    Article  CAS  Google Scholar 

  6. Mulzer, J., Altmann, K.-H., Höfle, G., Müller, R., and Prantz, K., C. R. Chim., 2008, vol. 11, p. 1336. https://doi.org/10.1016/j.crci.2008.02.005

    Article  CAS  Google Scholar 

  7. Lee, F.Y., Bovzilleri, R., Fairchild, C.R., Kamath, A., Smykla, R., Kramer, R., and Vite, G., Cancer Chemother Pharmacol,, 2008, vol. 63, p. 157. https://doi.org/10.1007/s00280-008-0724-8

    Article  CAS  Google Scholar 

  8. Biswas, K., Lin, H., Njardarson, J.T., Chappel, M.D., Chou, T.-C., Guan, Y., Tong, W.P., He, L., Horwitz, S.B., and Danishefsky, S.J., J. Am. Chem. Soc., 2002, vol. 124, p. 9825. https://doi.org/10.1021/ja0262333

    Article  CAS  PubMed  Google Scholar 

  9. Scholl, M., Ding, S., Lee, C.W., and Grubbs, R.H., Org. Lett., 1995, vol. 1, p. 953. https://doi.org/10.1021/ol990909q

    Article  CAS  Google Scholar 

  10. Scholl, M., Trnka, T.M., Morgan, J.P., and Grubbs, R.H., Tetrahedron Lett., 1999, vol. 40, p. 2247. https://doi.org/10.1016/S0040-4039(99)00217-8

    Article  CAS  Google Scholar 

  11. Valeev, R.F., Bikzhanov, R.F., Yagafarov, N.Z., and Miftakhov, M.S., Tetrahedron, 2012, vol. 68, p. 6868. https://doi.org/10.1016/j.tet.2012.06.020

    Article  CAS  Google Scholar 

  12. Valeev, R.F., Bikzhanov, R.F., and Miftakhov, M.S., Russ. J. Org. Chem., 2015, vol. 51, p. 660. https://doi.org/10.1134/S1070428015050139

    Article  CAS  Google Scholar 

  13. De Mico, A., Margarita, R., Parlanti, L., Vescovi, A., and Piancatelli, G., J. Org. Chem., 1997, vol. 62, p. 6974. https://doi.org/10.1021/jo971046m

    Article  CAS  Google Scholar 

  14. Blakemore, P.R., Cole, W.J., Kocienski, P.J., and Morley, A., Synlett, 1998, vol. 1998, no. 1, p. 26. https://doi.org/10.1055/s-1998-1570

    Article  Google Scholar 

  15. Valeev, R.F., Sunagatullina, G.R., and Miftakhov, M.S., Russ. J. Org. Chem., 2017, vol. 53, p. 1687. https://doi.org/10.1134/S1070428017110136

    Article  CAS  Google Scholar 

  16. Valeev, R.F., Sunagatullina, G.R., Loza, V.V., and Miftakhov, M.S., Russ. J. Org. Chem., 2018, vol. 54, p. 1548. https://doi.org/10.1134/S1070428018100172

    Article  CAS  Google Scholar 

  17. Evans, D.A., Ennis, M.D., and Mathre, D.J., J. Am. Chem. Soc., 1982, vol. 104, p. 1737. https://doi.org/10.1021/ja00370a050

    Article  CAS  Google Scholar 

  18. Bull, S.D., Davies, S.G., Jones, S., and Sanganee, H.J., J. Chem. Soc., Perkin Trans. 1, 1999, p. 387. https://doi.org/10.1039/A809715A

  19. Kotha, S. and Mandal, K., Eur. J. Org. Chem., 2006, vol. 2006, no. 23, p. 5387. https://doi.org/10.1002/ejoc.200600549

    Article  CAS  Google Scholar 

  20. Sytniczuk, A., Dabrowski, M., Banach, L., Urban, M., Czarnocka–Sniadala, S., Milewski, M., Kajetanowicz, A., and Grela, K., J. Am. Chem. Soc., 2018, vol. 140, p. 8895. https://doi.org/10.1021/jacs.8b04820

    Article  CAS  PubMed  Google Scholar 

  21. Inanaga, J., Kirata, K., Saeki, H., Katsuki, T., and Yamaguchi, M., Bull. Chem. Soc. Jpn., 1979, vol. 52, p. 1989. https://doi.org/10.1246/bcsj.52.1989

    Article  CAS  Google Scholar 

  22. Mukaiyama, T., Usui, M., Shimada, E., and Saigo, K., Chem. Lett., 1975, vol. 4, p. 1045. https://doi.org/10.1246/cl.1975.1045

    Article  Google Scholar 

  23. Kocienski, P.G., Protecting Groups, Stuttgart: Thieme, 1994, p. 129.

Download references

ACKNOWLEDGMENTS

The spectral studies were performed using the facilities of the Chemistry joint center (Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was financially supported by the Ministry of Science and Higher Education of the Russian Federation (program “Directed Syntheses of Natural and Unnatural Biologically Active Compounds and Design of New Structures for Optoelectronics”; state assignment nos. AAAAA20-120012090021-4, AAAA-A17-117011910032-4) and by the Russian Foundation for Basic Research (project no. 20-33-90039 Aspiranty).

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    R. F. Valeev, G. R. Sunagatullina, V. V. Loza, A. N. Lobov & M. S. Miftakhov

Authors
  1. R. F. Valeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. R. Sunagatullina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Loza
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. N. Lobov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. S. Miftakhov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. S. Miftakhov.

Ethics declarations

The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 6, pp. 802–819 https://doi.org/10.31857/S0514749221060033.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Valeev, R.F., Sunagatullina, G.R., Loza, V.V. et al. Synthesis of a New 10,11-Didehydro Analog of Epothilone D. Russ J Org Chem 57, 889–904 (2021). https://doi.org/10.1134/S1070428021060038

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021060038

Keywords:

Search

Navigation