Chemistry of Heterocyclic Compounds

, Volume 51, Issue 7, pp 613–620 | Cite as

Diazonamide synthetic studies. Reactivity of N-unsubstituted benzofuro[2,3-b]indolines

  • Ilga Mutule
  • Toms Kalnins
  • Edwin Vedejs
  • Edgars SunaEmail author

Benzofuro[2,3-b]indolines undergo ring opening in the presence of base to generate 3H-indolines. The latter can rearrange into 3-arylindoles through an intramolecular transfer of the methoxycarbonyl moiety from quaternary carbon to oxygen of phenol. The intermediate 3H-indolines can be isolated upon DMAP-catalyzed O-acylation of the phenol moiety with Boc2O.


diazonamide DMAP hemiaminal indole 3H-indoline 


We thank European Social Fund (project No. 1DP/ for financial support of this research. E. Vedejs thanks InnovaBalt project for funding.


  1. 1.
    For review on synthesis of diazonamide A, see: Lachia, M.; Moody, C. Nat. Prod. Rep. 2008, 25, 227.Google Scholar
  2. 2.
    Cruz-Monserrate, Z.; Vervoort, H. C.; Bai, R.; Newman, D. J.; Howell, S. B.; Los, G.; Mullaney, J. T.; Williams, M. D.; Pettit, G. R.; Fenical, W.; Hamel, E. Mol. Pharmacol. 2003, 63, 1273.CrossRefGoogle Scholar
  3. 3.
    For review, see: Beaud, R.; Tomakinian, T.; Denizot, N.; Pouilhès, A.; Kouklovsky, C.; Vincent, G. Synlett 2015, 26, 432.Google Scholar
  4. 4.
    (a) Tomakinian, T.; Kouklovsky, C.; Vincent, G. Synlett 2015, 26, 1269. (b) Ding, H.; DeRoy, P. L.; Perreault, C.; Larivée, A.; Siddiqui, A.; Caldwell, C. G.; Harran, S.; Harran, P. G. Angew. Chem., Int. Ed. 2015, 54, 4818. (c) Tomakinian, T.; Guillot, R.; Kouklovsky, C.; Vincent, G. Angew. Chem., Int. Ed. 2014, 53, 11881. (d) Liao, L.; Shu, C.; Zhang, M.; Liao, Y.; Hu, X.; Zhang, Y.; Wu, Z.; Yuan, W.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 10471. (e) Shu, C.; Liao L.-H.; Liao Y.-J.; Hu, X.-Y.; Zhang, Y.-H.; Yuan, W.-C.; Zhang, X.-M. Eur. J. Org. Chem. 2014, 4467. (f) Denizot, N.; Pouilhès, A.; Cucca, M.; Beaud, R.; Guillot, R.; Kouklovsky, C.; Vincent, G. Org. Lett. 2014, 16, 5752. (g) Zhao, J.-C.; Yu, S.-M.; Liu, Y.; Yao, Z.-J. Org. Lett. 2013, 15, 4300. (h) Beaud, R.; Guillot, R.; Kouklovsky, C.; Vincent, G. Angew. Chem., Int. Ed. 2012, 51, 12546.Google Scholar
  5. 5.
    (a) Zajac, M. A.; Vedejs, E. Org. Lett. 2004, 6, 237. (b) Peris, G.; Vedejs, E. J. Org. Chem. 2015, 80, 3050.Google Scholar
  6. 6.
    Poriel, C.; Lachia, M.; Wilson, C.; Davies, J. R.; Moody, C. J. J. Org. Chem. 2007, 72, 2978.CrossRefGoogle Scholar
  7. 7.
    Mutule, I.; Joo, B.; Medne, Z.; Kalnins, T.; Vedejs, E.; Suna, E. J. Org. Chem. 2015, 80, 3058.CrossRefGoogle Scholar
  8. 8.
    Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141.CrossRefGoogle Scholar
  9. 9.
    Basel, Y.; Hassner, A. J. Org. Chem. 2000, 65, 6368.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Ilga Mutule
    • 1
  • Toms Kalnins
    • 1
  • Edwin Vedejs
    • 1
    • 2
  • Edgars Suna
    • 1
    Email author
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia
  2. 2.Department of ChemistryUniversity of MichiganAnn ArborU. S. A.

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