Elsevier

Tetrahedron

Volume 20, Issue 12, 1964, Pages 2927-2931
Tetrahedron

Terpenoids—LXI : Conversion of eudesmol to di- and tetrahydrocostol

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Abstract

Dihydro-β-eudesmol (IV), obtained by catalytic hydrogenation of β-eudesmol (II), on pyrolysis via the benzoate gives dihydro-β-selinene (V). Its epoxyderivative (VI) is converted on treatment with acetic acid to the hydroxy acetate (VII), the benzoate of which on pyrolysis, followed by saponification, affords dihydrocostol (XI), converted by hydrogenation to tetrahydrocostol (XII). The alcohol (XI) is not identical with agarol to which the same stereoformula has been assigned previously. These results would necessitate a re-examination of the structure and stereochemistry of agarol which has already been undertaken.

References (10)

  • A.J. Birch et al.

    Austr. J. Chem.

    (1954)
  • T.C. Jain
    (1960)
  • F.J. McQuillin et al.

    J. Chem. Soc.

    (1956)
    E. Von Rudloff

    Chem. & Ind.

    (1962)
  • R.B. Bates et al.

    Chem. & Ind.

    (1962)
  • P. Rudmann

    Chem. & Ind.

    (1964)
There are more references available in the full text version of this article.

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Communication No. 709 from the National Chemical Laboratory, Poona-8, India.

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