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Synthesis of steroid compounds and related substances

Communication: XXI. Condensation of 3,4,4a,5,8,8a-hexahydro-8a-methyl-1-vinylnaphthalene withα,β-unsaturated cyclic ketones. synthesis of steroid ketones derived from hydrogenated cyclopenta[a]phenanthrene and chrysene

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    The complete syntheses of a number of new steroid ketones have been effected by condensation of 3,4,4a, 5,8,8a-hexahydro-8a-methyl-1-vinylnaphthalene (V) with 2-methyl -2-cyclopenten-1-one (VII), 2,4-dimethyl-2-cyclopentene-l-one (VIII), 2-cyclohexen-l-one (IX), 2-methyl-2-cyclohexen-l-one (X), p-benzoquinone (XI), and 3,5-dimethyl-3-cyclopentene-1,2-dione (XII). The steroid ketones obtained by the condensation of the triene V with the cyclopentenones VII and VIII have the so-called *inverted structure, and the main product of the condensation of the triene V with citraconic anhydride has the same structure.

  2. 2.

    It has been shown that displacement of the double bond irr the 9(11) position readily occurs when steroid ketones are heated with hydrochloric acid or are shaken in acetic acid solution in presence of a platinum catalyst.

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Authors and Affiliations

  1. Institute of Organic Chemistry of the USSR Academy of Sciences, USSR

    I. N. Nazarov, L. I. Shmonina & I. V. Torgov

Authors
  1. I. N. Nazarov
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  2. L. I. Shmonina
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  3. I. V. Torgov
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Nazarov, I.N., Shmonina, L.I. & Torgov, I.V. Synthesis of steroid compounds and related substances. Russ Chem Bull 2, 955–968 (1953). https://doi.org/10.1007/BF01167543

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  • DOI: https://doi.org/10.1007/BF01167543

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