Elsevier

Tetrahedron Letters

Volume 52, Issue 35, 31 August 2011, Pages 4512-4514
Tetrahedron Letters

Synthesis of BCD tricyclic analogues of the novel cardiac glycoside rhodexin A

https://doi.org/10.1016/j.tetlet.2011.06.114Get rights and content

Abstract

A concise synthesis of novel cardiac glycoside analogues of rhodexin A, 14 and 24, having the BCD tricyclic system is described. The key constructive step is an inverse-electron demand Diels–Alder reaction of the silyl enol ether 4 and the 2-acetyldiene, 7 and 15.

Graphical abstract

A concise synthesis of the two BCD tricyclic analogues 14 and 24 of the cardiac glycoside rhodexin A is described.

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Acknowledgments

HVC gratefully acknowledges the National Institutes of Health for support via Grant No. GM08496.

References and notes (16)

  • K. Suenaga et al.

    Tetrahedron Lett.

    (1996)
  • M. Arnaud

    Compt. Rend. Acad.

    (1888)
    W.A. Jacobs et al.

    J. Biol. Chem.

    (1932)
    C. Tamm et al.

    Helv. Chim. Acta

    (1957)
    G. Volpp et al.

    Helv. Chim. Acta

    (1957)
    D.D. McIntyre et al.

    Can. J. Chem.

    (1990)
  • H. Nawa

    Proc. Japan Acad.

    (1951)
    K. Kikuchi et al.

    J. Pharmacol. Exp. Ther.

    (1964)
    C. Umebayashi et al.

    Biol. Pharm. Bull.

    (2003)
    T. Masuda et al.

    Biosci. Biotechnol., Biochem.

    (2003)
  • M.E. Jung et al.

    Angew. Chem., Int. Ed.

    (2002)
    M.E. Jung et al.

    Org. Lett.

    (2003)
    M.E. Jung et al.

    J. Org. Chem.

    (2003)
    M.E. Jung et al.

    Org. Lett.

    (2008)
    M.E. Jung et al.

    Org. Lett.

    (2011)
  • P.J. Parsons et al.

    Tetrahedron

    (1994)
  • A.B. Smith et al.

    Org. Lett.

    (2005)
  • F.J. Urban et al.

    Tetrahedron Lett.

    (1990)
  • A.S. MehannaG.B. Somberg J et al.

    J. Clin. Pharmacol.

    (1985)
    K.-O. Haustein

    Pharmacol. Ther.

    (1982)
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