Skip to main content
Log in

Functional divergency oriented synthesis of azoninones as the key intermediates for bioactive indolizidine alkaloids analogs

  • Research Article
  • Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

An Erratum to this article was published on 01 January 2005

Abstract

A functional divergency oriented synthetic approach to the azoninone (9-membered lactams), key intermediate for the indolizidine alkaloids library, using amide enolate induced aza-Claisen rearrangement has been achieved.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Burke, M. D. and Schreiber, S. L., A planning strategy for diversity-oriented synthesis.Angew. Chem., Int. Ed. Engl., 43, 46–58 (2004).

    Article  Google Scholar 

  • Castro, A. M. M., Claisen rearrangement over the past nine decades.Chem. Rev., 104, 2939–3002 (2004).

    Article  CAS  Google Scholar 

  • Coates, R. M., Rogers, B. D., Hobbs, S. J., Curran, D. P., and Peck, D. R., Synthesis and Claisen rearrangement of alkoxyallyl enol ethers. Evidence for a dipolar transition state.J. Am. Chem. Soc., 109, 1160–1170 (1987).

    Article  CAS  Google Scholar 

  • Diederich, M. and Nubbemeyer, U., Synthesis of optically-active 9-membered ring lactams by a zwitterionic, aza-Claisen reaction.Angew. Chem., Int. Ed. Engl., 34, 1026–1028 (1995).

    Article  CAS  Google Scholar 

  • Edstrom, E. D., New methodology for the synthesis of functionalized indolizidine and quinolizidine ring systems.J. Am. Chem. Soc., 113, 6690–6692 (1991).

    Article  CAS  Google Scholar 

  • Evans, P. A. and Holmes, A. B., Medium ring nitrogen heterocyles.Tetrahedron, 47, 9131–9166 (1991).

    Article  CAS  Google Scholar 

  • Guengerich, F. P. and Bronquist, H. P., InBioorganic Chemistry, Ed. Van Tameleon, E. E. Academic, New York, Vol 2, 97–109 (1979).

    Google Scholar 

  • Michael, J. P., Indolizidine and quinolizidine alkaloids.Nat. prod. Rep., 18, 520–542 (2001).

    Article  PubMed  CAS  Google Scholar 

  • Molyneux, R. J., Tropea, J. E., and Elbein, A. D., 7-Deoxy-6-epi- castanospermine, a trihydroxyindolizidine alkaloid glycosidase inhibitor from Castanospermum australe.J. Nat. Prod., 53, 609–614 (1990).

    Article  PubMed  CAS  Google Scholar 

  • Nubbemeyer, U., Synthesis of medium-sized ring lactams.Top. Curr. Chem., 216, 125–196 (2001).

    Article  CAS  Google Scholar 

  • Pereira, S. and Srebnik, M., The Ireland-Claisen rearrangement.Aldrichimica Acta, 26, 17–29 (1993)

    CAS  Google Scholar 

  • Sudau, A. and Nubbemeyer, U., Unusual diastereoselection in the synthesis of 9-membered ring lactams and conformation-controlled transannular reactions to generate optically active indolizidinones.Angew. Chem. Int. Ed. Engl., 37, 1140–1143 (1998).

    Article  CAS  Google Scholar 

  • Suh, Y.-G., Kim, S.-A., Jung, J.-K., Shin, D.-Y., Min, K.-H., Koo, B.-A., and Kim, H.-S., Asymmetric Total Synthesis of Fluvirucinine A1.Angew. Chem. Int. Ed. Engl., 38, 3545–3547 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Suh, Y.-G., Lee, J.-Y., Kim, S.-A., and Jung, J.-K., A new ring expansion reaction of 1-acyl-2-vinylpiperidine and 1-acyl-2- vinylpiperazinevia aza-Claicen rearrangement of amide enolate.Synth. Commun., 26, 1675–1680 (1996).

    Article  CAS  Google Scholar 

  • Tsunoda, T., Tatsuki, S., Shiraishi, Y., Akasaka, M., and Ito, S., Asymmetric aza-Claisen rearrangement of glycolamide and glycinamide enolates. Synthesis of optically active a-hydroxy and a-amino acids.Tetrahedron Lett., 34, 3297–3300 (1993).

    Article  CAS  Google Scholar 

  • Vedejs, E. and Gingras, M., Aza-Claisen rearrangements initiated by acid-catalyzed Michael addition.J. Am. Chem. Soc., 116, 579–588 (1994).

    Article  CAS  Google Scholar 

  • Yet, L., Metal-mediated synthesis of medium-sized rings.Chem. Rev., 100, 2963–3007 (2000).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Young -Ger Suh.

Additional information

An erratum to this article is available at http://dx.doi.org/10.1007/BF02975148.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jung, J.K., Choi, N.S. & Suh, Y.G. Functional divergency oriented synthesis of azoninones as the key intermediates for bioactive indolizidine alkaloids analogs. Arch Pharm Res 27, 985–989 (2004). https://doi.org/10.1007/BF02975418

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02975418

Key words

Navigation