Elsevier

Tetrahedron Letters

Volume 53, Issue 32, 8 August 2012, Pages 4100-4103
Tetrahedron Letters

The synthesis of hydroxy-pyrrolizidines and indolizidines from cyclopropenones: towards hyacinthacines, australines and jenamidines

https://doi.org/10.1016/j.tetlet.2012.05.117Get rights and content

Abstract

The reaction of cyclic imines (1-pyrrolines and piperideines) with a cyclopropenone leads to pyrrolizidines and indolizidines, respectively, each with a hydroxy group on the carbon atom at the bridgehead. The cyclopropenone functions as an all-carbon 1,3-dipole equivalent towards the cyclic imine in this reaction, and the cyclic imines used include polyhydroxylated systems, thus allowing access to australine, alexine and hyacinthacine type compounds. The pyrrolizidine products contain the core of the jenamidine and bohemamine natural products, which are of interest as cell-proliferation inhibitors and cell–cell adhesion inhibitors.

Section snippets

Acknowledgments

This work was supported by the University of Huddersfield Studentships (to V.V.R.K. and M.I.Q.). We thank Dr Neil McLay, University of Huddersfield, for NMR and mass spectroscopic support, Dr Craig Rice, University of Huddersfield, for X-ray crystallographic studies, and the EPSRC national mass spectrometry service, University of Wales, Swansea for HRMS.

References and notes (32)

  • B. Macchi et al.

    Glycobiology

    (2010)
    B.G. Winchester

    Tetrahedron: Asymmetry

    (2009)
    P. Compain et al.

    Curr. Top. Med. Chem.

    (2003)
    Z. Yu et al.

    J. Med. Chem.

    (2007)
    P. CompainE.M. Sanchez-Fernandez et al.

    Chem. Commun.

    (2010)
  • N.T. Patil et al.

    Tetrahedron Lett.

    (2005)
    A.B. Smith et al.

    J. Org. Chem.

    (2006)
    S. Nukui et al.

    J. Org. Chem.

    (1995)
    J.P. Michael et al.

    Synlett

    (1996)
    N.B. Kondekar et al.

    Synthesis

    (2010)
    N. Toyooka et al.

    Tetrahedron

    (2005)
    T.H. Jones et al.

    J. Nat. Prod.

    (2007)
  • D.D. Buechter et al.

    J. Nat. Prod.

    (1987)
  • G. Baxter et al.

    Synlett

    (1991)
  • G.P. Claxton et al.

    Org. Synth.

    (1988)
    M.F. Grundon et al.

    J. Chem. Soc.

    (1963)
    F.E. Scully

    J. Org. Chem.

    (1980)
  • C.M. Vanos et al.

    Angew. Chem., Int. Ed.

    (2011)
    B.D. Kelly et al.

    Org. Lett.

    (2011)
    C.M. Vanos et al.

    Chem. Sci.

    (2010)
    D.J. Hardee et al.

    J. Am. Chem. Soc.

    (2010)
  • B.L. Stocker et al.

    Eur. J. Org. Chem.

    (2010)
    J.W. Daly et al.

    J. Nat. Prod.

    (2005)
  • J.P. Michael

    Nat. Prod. Rep.

    (2008)
  • X.-K. Liu et al.

    J. Org. Chem.

    (2011)
    P.V. Reddy et al.

    Org. Biomol. Chem.

    (2008)
    E.A. Brock et al.

    Org. Lett.

    (2011)
  • T. Sengoku et al.

    Tetrahedron

    (2008)
    P.V. Reddy et al.

    Synlett

    (2009)
    A. Kato et al.

    Carbohydr. Res.

    (1999)
  • T.J. Donohoe et al.

    Org. Lett.

    (2008)
    W.H. Pearson et al.

    J. Org. Chem.

    (2000)
    T. Ritthiwigrom et al.

    J. Org. Chem.

    (2010)
    M. Takahashi et al.

    Tetrahedron

    (2008)
    P. Gilles et al.

    Org. Lett.

    (2012)
  • E.G. Bowen et al.

    Org. Lett.

    (2010)
    J. Louvel et al.

    Eur. J. Org. Chem.

    (2010)
    T. Ritthiwigrom et al.

    Tetrahedron

    (2010)
    G. Liu et al.

    Chem. Eur. J.

    (2010)
    A.M.P. Koskinen et al.

    Tetrahedron

    (2009)
  • T. Tokuyama et al.

    Tetrahedron

    (1986)
  • T.W. Doyle et al.

    J. Org. Chem.

    (1980)
    T.S. Bugni et al.

    J. Nat. Prod.

    (2006)
  • Cited by (0)

    View full text