Skip to main content
SpringerLink
Log in

Macrocyclisation of 2-(5-(2-hydroxyethyl)furan-2-yl)acetic acid model compounds of nonactic acid

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The macrocyclisation of hydroxyethylfuranyl acetic acid and of dehydrogenated model compounds of nonactic acid was investigated to develop a facile synthesis of nonactin analogues. By applying the Yamagushi macrocyclisation to our ω-hydroxyacids, we were able to isolate a mixture of di-, tri-, tetra- and pentameric macrocycles.

Graphical abstract

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
Fig. 1

Similar content being viewed by others

References

  1. Corbaz R, Ettinger L, Gaumann E, Keller-Schlierlein W, Kradolfer F, Neipp L, Prelog V, Zahner H (1955) Helv Chim Acta 38:1445

    Article  CAS  Google Scholar 

  2. Gerlach H, Oertle K, Thalmann A, Servi S (1975) Helv Chim Acta 58:2036

    Article  CAS  Google Scholar 

  3. Schmidt U, Gombos J, Haslinger E, Zak H (1976) Chem Ber 109:2628

    Article  CAS  Google Scholar 

  4. Bartlett PA, Meadows JD, Ottow E (1984) J Am Chem Soc 106:5304

    Article  CAS  Google Scholar 

  5. Lee JY, Kim BH (1996) Tetrahedron 52:571

    Article  CAS  Google Scholar 

  6. Fleming I, Ghosh SK (1998) J Chem Soc Perkin Trans 1:2733

    Article  Google Scholar 

  7. Wu Y, Sun Y-P (2006) Org Lett 8:2831

    Article  CAS  Google Scholar 

  8. Nikodinovic J, Dinges JM, Bergmeier SC, McMills MC, Wright DL, Priestley ND (2006) Org Lett 8:443

    Article  CAS  Google Scholar 

  9. Loiseau F, Simone J-M, Carcache D, Bobal P, Neier R (2007) Monatsh Chem 138:121

    Article  CAS  Google Scholar 

  10. Simone J-M, Loiseau F, Carcache D, Bobal P, Jeanneret-Gris J, Neier R (2007) Monatsh Chem 138:131

    Article  CAS  Google Scholar 

  11. Simone J-M, Loiseau F, Carcache D, Bobal P, Jeanneret-Gris J, Neier R (2007) Monatsh Chem 138:141

    Article  CAS  Google Scholar 

  12. Hanessian S, Liak TJ, Vanasse B (1981) Synthesis 396

  13. Schmidt U, Werner J (1986) Synthesis 986

  14. Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M (1979) Bull Chem Soc Jpn 52:1989

    Article  CAS  Google Scholar 

  15. Brady PA, Sanders JKM (1997) J Chem Soc Perkin Trans 1:3237

    Article  Google Scholar 

  16. De Sousa Healy M, Rest AJ (1981) J Chem Soc Chem Commun 4:149

    Article  Google Scholar 

Download references

Acknowledgments

The NMR spectra (400 MHz) were measured by Heinz Bursian and Dr. Claude Saturnin, the mass spectra by Dr. Manuel Tharin and Dr. Bernard Jean-Denis. We thank the University of Neuchâtel and the Swiss National Science Foundation for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Neuchâtel, Avenue Bellevaux 51, 2007, Neuchâtel, Switzerland

    Carine Eng, Jean-Mary Simone, Akane Hartenbach, François Loiseau & Reinhard Neier

Authors
  1. Carine Eng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jean-Mary Simone
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Akane Hartenbach
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. François Loiseau
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Reinhard Neier
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Reinhard Neier.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Eng, C., Simone, JM., Hartenbach, A. et al. Macrocyclisation of 2-(5-(2-hydroxyethyl)furan-2-yl)acetic acid model compounds of nonactic acid. Monatsh Chem 140, 349–354 (2009). https://doi.org/10.1007/s00706-008-0031-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0031-4

Keywords

Search

Navigation