Synthesis and anti-herpes activity of some a-ring functionalized dehydroabietane derivatives

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Abstract

Dehydroabietic acid 5 was converted to the exocyclic olefin 7 by applying the Barton decarboxylation protocol. The latter served as key intermediate for the stereoselective synthesis of a variety of ring-A functionalized derivatives. Compounds 13 and 16 turned out to be active against the herpes virus (HSV-2) in the standard plaque assay and seem to interfere with an early event in viral replication.

Dehydroabietic acid 5 was converted to the exo-cyclic olefin 7 which was used as a versatile intermediate in the synthesis of A-ring hydroxylated compounds such as 13 and 16 which showed HSV-2 inhibitory activity in the standard plaque assay.

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References (10)

  • K. Hayashi et al.

    Antiviral Research

    (1988)
  • J.W. Huffman et al.

    J. Org. Chem.

    (1963)
  • E.J. Cochran et al.

    Tetrahedron Lett.

    (1989)
  • R.A. Bucknall et al.

    Antimicrob. Agents. Chemother.

    (1973)
    M. Ohashi et al.

    Biochem. Biophys. Res. Commun.

    (1978)
    G. Pedrali-Noy et al.

    Biochem. Biophys. Res. Commun.

    (1979)
  • K. Nakayama et al.

    J. Org. Chem.

    (1984)
There are more references available in the full text version of this article.

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