Elsevier

Tetrahedron Letters

Volume 48, Issue 9, 26 February 2007, Pages 1571-1575
Tetrahedron Letters

A practical method for the synthesis of pyrrolizidine, indolizidine and pyrroloazepinolizidine nucleus

https://doi.org/10.1016/j.tetlet.2007.01.015Get rights and content

Abstract

The alkylation of α,ω-dibromoalkanes, with the sodium salt of succinimide, followed by the reduction with sodium borohydride gives the respective N-ω-bromoalkyl-5-hydroxy-2-pyrrolidinones. These substrates are precursors of N-acyliminium ions under acidic conditions. The condensation of these intermediates with ethyl malonate in the presence of TiCl4 and diisopropylethylamine following the intramolecular cyclization provides a convenient route to substituted pyrrolizidinone, indolizidinone and pyrroloazepinolizidinone nucleus in a good yield.

Section snippets

Acknowledgments

Financial support for this research from ‘Coordinación de Investigación y Estudios Avanzados de la Universidad Autónoma del Estado de México’ (1863/2004) and (1980/2004) is gratefully acknowledged. The authors wish to thank Professor Joseph M. Muchowski from UNAM for helpful discussions and his interest in our work.

References and notes (25)

  • Y. Chen et al.

    J. Org. Chem.

    (1994)
    M. Gerspacher et al.

    J. Org. Chem.

    (1991)
    T.G. Back et al.

    Org. Lett.

    (1999)
  • R.B. Clark et al.

    Org. Lett.

    (1999)
    A.R. DeFaria et al.

    J. Org. Chem.

    (2002)
  • J.W. Daly

    J. Nat. Prod.

    (1998)
    W.H. Pearson et al.

    J. Org. Chem.

    (2000)
  • H. Komatzu et al.

    J. Med. Chem.

    (2001)
  • H.W. Pinnick et al.

    J. Org. Chem.

    (1978)
    E. Dietrich et al.

    J. Org. Chem.

    (2003)
  • M. Pourashraf et al.

    J. Org. Chem.

    (2000)
    M. Lombardo et al.

    Tetrahedron

    (2000)
    H.K. Lee et al.

    J. Org. Chem.

    (2003)
  • P.A. Jacobi et al.

    J. Am. Chem. Soc.

    (2000)
    C.M. Marson et al.

    J. Org. Chem.

    (2003)
  • K. Burges et al.

    Tetrahedron

    (1992)
    X.L.M. Despinoy et al.

    Tetrahedron

    (2000)
    A.E. Nerm

    Tetrahedron

    (2000)
    S.E. Denmark et al.

    J. Org. Chem.

    (2000)
  • T.G. Back et al.

    J. Org. Chem.

    (2000)
    N.A. Khatry et al.

    J. Am. Chem. Soc.

    (1981)
  • T. Suami et al.

    Chem. Lett.

    (1984)
    W.H. Pearson et al.

    J. Org. Chem.

    (1996)
  • H. Setoi et al.

    J. Org. Chem.

    (1985)
  • A. Sudau et al.

    J. Org. Chem.

    (2000)
  • Cited by (0)

    View full text