Elsevier

Tetrahedron Letters

Volume 50, Issue 37, 16 September 2009, Pages 5277-5279
Tetrahedron Letters

Expedient asymmetric synthesis of a functionalized 5-7-6 fused tricyclic skeleton present in caribenol A through ring opening-ring closing metathesis of a norbornene derivative

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Abstract

A concise approach towards the synthesis of the highly biologically active terpenoid caribenol A is described involving sequential aldol condensation-ring opening-ring closing metathesis of a norbornene derivative.

Graphical abstract

A concise synthesis of the tricyclic core structure present in highly biologically active terpenoids caribenol A is described using RO-RCM of a norbornene derivative.

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Acknowledgements

Financial support from the Department of Science and Technology, Government of India through Ramanna Fellowship to S.G. is gratefully acknowledged. S.M. thanks CSIR, New Delhi for a senior research fellowship.

References and notes (9)

  • E.J. Corey et al.

    Tetrahedron Lett.

    (1997)
    M. Kawatsura et al.

    Synlett

    (1997)
  • X. Wei et al.

    J. Org. Chem.

    (2007)
  • B.R. Bloom et al.

    Science

    (1992)
  • O. Arjona et al.

    Eur. J. Org. Chem.

    (2003)
    S. Blechert et al.

    Chem. Asian J.

    (2007)
    J.R. Stille et al.

    J. Org. Chem.

    (1990)
    M.F. Scheeinder et al.

    Angew. Chem., Int. Ed.

    (1997)
    R. Stragies et al.

    Synlett

    (1998)
    G.S. Weatherhead et al.

    J. Am. Chem. Soc.

    (2000)
    H. Hagiwara et al.

    Tetrahedron

    (2002)
    A.C. Hart et al.

    J. Am. Chem. Soc.

    (2006)
    S. Maechling et al.

    Tetrahedron Lett.

    (2006)
There are more references available in the full text version of this article.

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