Skip to main content
SpringerLink
Log in

Synthesis and Isomerization of the 2-Methyl Enal Fragment of Acyclic Precursors to 9,11-Diene Analogs of Epothilones

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

Abstract

Yamaguchi esterification of (2Z,5S,6E)-5-(hydroxymethyl)-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienal with (2R,5R,6S,7S)-2-(methoxymethoxy)-3,3,5,7-tetramethyl-4-oxo-9-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl-6-[(triethylsilyl)oxy]nonanoic acid afforded the expected acyclic ester. Acid- and base-catalyzed Z,E-isomerization in the 2-methyl enal fragment of acyclic precursors was revealed.

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

Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Cao, Y.-N., Zheng, L.-L., Wang, D., Liang, X.-X., Gao, F., and Zhou, X.-L., Eur. J. Med. Chem., 2018, vol. 143, p. 806. https://doi.org/10.1016/j.ejmech.2017.11.062

    Article  CAS  PubMed  Google Scholar 

  2. Valeev, R.F., Sunagatullina, G.R., and Biglova, R.Z., Mendeleev Commun., 2018, vol. 28, p. 587. https://doi.org/10.1016/jmencom.2018.11.007

    Article  CAS  Google Scholar 

  3. Jakubec, P., Cockfield, D.M., and Dixon, D.J., J. Am. Chem. Soc., 2009, vol. 46, p. 16632. https://doi.org/10.1021/ja908399s

    Article  CAS  Google Scholar 

  4. 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 

  5. Valeev, R.F., Sunagatullina, G.R., and Miftakhov, M.S., Russ. J. Org. Chem., 2019, vol. 55, p. 1439. https://doi.org/10.1134/S1070428019090264

    Article  CAS  Google Scholar 

  6. 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 

  7. Dash, U., Sengupta, S., and Sim, T., Eur. J. Org. Chem., 2015, vol. 2015, p. 3963. https://doi.org/10.1002/ejoc.201500380

    Article  CAS  Google Scholar 

  8. Blakemore, P.R., Ho, D.K.H., and Nap, W.M., Org. Biomol. Chem., 2005, vol. 3, p. 1365. https://doi.org/10.1039/B500713E

    Article  CAS  PubMed  Google Scholar 

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 performed in the framework of state assignment (project nos. AAAA-A17-117011910032-4, AAAA-A20-120012090021-4).

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 & 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. M. S. Miftakhov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. F. Valeev.

Ethics declarations

The authors declare no conflict of interest.

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. & Miftakhov, M.S. Synthesis and Isomerization of the 2-Methyl Enal Fragment of Acyclic Precursors to 9,11-Diene Analogs of Epothilones. Russ J Org Chem 56, 1140–1145 (2020). https://doi.org/10.1134/S1070428020070039

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020070039

Keywords:

Search

Navigation