Skip to main content
SpringerLink
Log in

Rearrangement of Epoxide Derivatives Semisynthesized from β-Himachalene using Lewis and Bronsted Acids Catalysis

  • Published:
Chemistry of Natural Compounds Aims and scope

The acid-catalyzed rearrangement of epoxides 3a, 4a, 6a, and 7a derived from β-himachalene, the major constituent of Cedrus atlantica essential oil, has been studied using various Lewis and Bronsted acids. Several new enantiomerically pure ketones were obtained in good yields and high selectivities. All products obtained were fully characterized by 1H and 13C NMR, and the mechanistic explanations for their formation were proposed.

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 1.
Scheme 2.
Scheme 3.
Scheme 4.

Similar content being viewed by others

References

  1. J. El Karroumi, A. El Haib, E. Manoury, A. Benharref, J. C. Daran, M. Gouygou, and M. Urrutigoity, J. Mol. Catal. A: Chem., 401, 18 (2015).

    Article  CAS  Google Scholar 

  2. E. V. Gusevskaya, J. Jimenez-Pinto, and A. Borner, ChemCatChem, 6, 382 (2014).

    Article  CAS  Google Scholar 

  3. J. G. da Silva, H. J. V. Barros, A. Balanta, A. Bolanos, M. L. Novoa, M. Reyes, R. Contreras, J. C. Bayon, E. V. Gusevskaya, and E. N. dos Santos, Appl. Catal. A-Gen., 326, 219 (2007).

    Article  Google Scholar 

  4. F. E. Koehn and G. T. Carter, Nat. Rev. Drug Discov., 4, 206 (2005).

    Article  CAS  Google Scholar 

  5. G. Jaritz and M. Bounejmate, Production et Utilisation des Cultures Fourragères au Maroc, INRA, Rabat, 1997.

    Google Scholar 

  6. M. Loubidi, D. Agustin, A. Benharref, and R. Poli, C. R. Chim., 17, 549 (2014).

    Article  CAS  Google Scholar 

  7. A. Chekroun, A. Jarid, A. Benharref, and A. Boutalib, J. Org. Chem., 65, 4431 (2000).

    Article  CAS  Google Scholar 

  8. E. Lassaba, H. Eljamili, A. Benharref, A. Chiaroni, C. Riche, and M. Pierrot, Bull. Soc. Chim. Belg., 106, 773 (1997).

    CAS  Google Scholar 

  9. A. Auhmani, E. Kossareva, H. Eljamili, M. Reglier, M. Pierrot, and A. Benharref, Synth. Commun., 32, 699 (2002).

    Article  CAS  Google Scholar 

  10. M. Daoubi, R. Hernandez-Galan, A. Benharref, and I. G. Collado, J. Agric. Food Chem., 53, 6673 (2005).

    Article  CAS  Google Scholar 

  11. A. El Haib, A. Benharref, S. Parres-Maynadie, and E. Manoury, J.-C. Daran, M. Urrutigoity, and M. Gouygou, Tetrahedron: Asymmetry, 21, 1272 (2010).

    Article  Google Scholar 

  12. f

  13. M. Gouygou and M. Urrutigoity, Comprehensive Organic Synthesis II, Vol. 3, Elsevier, Amsterdam, 2014, p. 757.

    Book  Google Scholar 

  14. E. Erturk, M. Gollu, and A. S. Demir, Tetrahedron, 66, 2373 (2010).

    Article  CAS  Google Scholar 

  15. J. Meinwald, S. S. Labana, and M. S. Chadha, J. Am. Chem. Soc., 85, 582 (1963).

    Article  CAS  Google Scholar 

  16. N. Mazoir, M. Dakir, M. Tebbaa, M. Loughzail, and A. Benharref, Tetrahedron Lett., 57, 278 (2016).

    Article  CAS  Google Scholar 

  17. M. Moumou, A. El Hakmaoui, A. Benharref, and M. Akssira, Tetrahedron Lett., 53, 3000 (2012).

    Article  CAS  Google Scholar 

  18. M. Tebbaa, A. El Hakmaoui, A. Benharref, and M. Akssira, Tetrahedron Lett., 52, 3769 (2011).

    Article  CAS  Google Scholar 

  19. M. Dakir, F. El Hanbali, F. Mellouki, M. Akssira, A. Benharref, J. F. Qulez del Moral, and A. F. Barrero, Nat. Prod. Res., 19, 719 (2005).

    Article  CAS  Google Scholar 

  20. A. F. Barrero, J. F. Qulez del Moral, M. M. Herrador, J. F. Arteaga, M. Akssira, A. Benharref, and M. Dakir, Phytochemistry, 66, 105 (2005).

    Article  CAS  Google Scholar 

  21. T.-L. Ho and R. J. Chein, Helv. Chim. Acta, 89, 231 (2006).

    Article  CAS  Google Scholar 

  22. T. C. Joseph and S. Dev, Tetrahedron, 24, 3809 (1968).

    Article  CAS  Google Scholar 

  23. H. Eljamili, A. Auhmani, M. Dakir, E. Lassaba, A. Benharref, M. Pierrot, A. Chiaroni, and C. Riche, Tetrahedron Lett., 43, 6645 (2002).

    Article  CAS  Google Scholar 

  24. A. Auhmani, E. Kossareva, H. El Jamili, M. Reglier, M. Pierrot, and A. Benharref, J. Chem. Crystallogr., 30, 525 (2000).

    Article  CAS  Google Scholar 

  25. M. Dakir, A. Auhmani, M. Y. A. Itto, N. Mazoir, M. Akssira, M. Pierrot, and A. Benharref, Synth. Commun., 34, 2001 (2004).

    Article  CAS  Google Scholar 

  26. A. Oukhrib, A. Benharref, M. Saadi, M. Berraho, and L. El Ammari, Acta Crystallogr. E, 69, o621 (2013).

    Article  Google Scholar 

  27. A. Benharref, L. El Ammari, D. Avignant, A. Oudahmane, and M. Berraho, Acta Crystallogr. E, 66, o3125 (2010).

    Article  CAS  Google Scholar 

  28. M. Zaki, A. Benharref, L. El Ammari, M. Saadi, and M. Berraho, Acta Crystallogr. E, 70, o444 (2014).

    Article  CAS  Google Scholar 

  29. M. Zaki, A. Benharref, J.-C. Daran, and M. Berraho, Acta Crystallogr. E, 70, o526 (2014).

    Article  CAS  Google Scholar 

  30. A. Benharref, J. El Karroumi, J.-C. Daran, and M. Berraho, Acta Crystallogr. E, 69, o1703 (2013).

    Article  CAS  Google Scholar 

  31. A. Benharref, M. Mazoir, J.-C. Daran, and M. Berraho, Acta Crystallogr. E, 69, o1777 (2013).

    Article  CAS  Google Scholar 

  32. F. Sbai, M. Dakir, A. Auhmani, H. El Jamili, M. Akssira, A. Benharref, A. Kenz, and M. Pierrot, Acta Crystallogr. C, 58, o518 (2002).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors wish to thank Prof. Moha Berraho and Jean-Claude Daran for X-ray crystallographic assistance.

Author information

Authors and Affiliations

  1. Laboratory of Organic Synthesis, Extraction and Valorization, Department of Chemistry, Faculty of Sciences Ain Chock, Hassan II University, Casablanca, Morocco

    Mohamed Dakir

  2. Department of Chemistry, Faculty of Sciences Semlalia, Cadi Ayyad University, Marrakech, Morocco

    Mustapha Ait Elhad, Abdelouahd Oukhrib, Noureddine Mazoir & Ahmed Benharref

  3. Laboratory of Plant Biotechnology and Ecosystem Valorisation, Faculty of Sciences, University Chouaib Doukkali, El Jadida, Morocco

    Noureddine Mazoir

Authors
  1. Mohamed Dakir
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mustapha Ait Elhad
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abdelouahd Oukhrib
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Noureddine Mazoir
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ahmed Benharref
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohamed Dakir.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2020, pp. 575–579.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dakir, M., Elhad, M.A., Oukhrib, A. et al. Rearrangement of Epoxide Derivatives Semisynthesized from β-Himachalene using Lewis and Bronsted Acids Catalysis. Chem Nat Compd 56, 663–669 (2020). https://doi.org/10.1007/s10600-020-03116-w

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-020-03116-w

Keywords

Search

Navigation