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Synthesis of steroid compounds and related substances Communication XX. Condensation of 3,4,4a,7,8,8a-hexahydro-4a-methyl-5-vinyl-2(1H)-naphthalenone and 3,4,4a,5,6,8a-hexahydro-8a-methyl-8-vinyl-2(1H)-naphthalenone with 2-cyclopenten-i-one, 2-methyl-2-cyclopenten-1-one, and 3,5-dimethyl-9-cyclopentene-1,2-dione

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Total syntheses of the steroid diketones IV and X of the cis-cis series have been effected by condensation of 3,4,4a,7,8,8a-hexahydro-4a-methyl-5-vinyl-2(1H)-naphthalenone (I) and 3,4,4a,5,6,6a-hexahyro-8a-methyl-8-vinyl-2(1H)-naphthalenone (II) with 2-methyl 2-cyclopenten-1-one (III). From the mixtures of isomers formed (IV and X), in each case three isomeric diketones were isolated, two of which, i.e., those formed in the greatest amount, have been shown to have “inverted” structures and to differ with respect to the spatial arrangement of substituents at C13-C14

  2. 2.

    3,4,4a,7,8,8a-Hexahydro-4a-methyl-5-vinyl-2(1H)-naphthalenone (I) has been condensed also with 2-cyclopenten-1-one (XI), and two isomeric steroid diketones (XII) have been isolated.

  3. 3.

    Condensation of the hexahydromethylvinyl-2(1H)-naphthalenone I with 3,5-dimethyl-3cyclopentene-1,2-dione (XIII) yielded the steroid triketone XIV, which very readily isomerizes into the diketo enol XV.

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Literature cited

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Authors and Affiliations

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

    I. N. Nazarov, G. P. Verkholetova, I. V. Torgov, I. I. Zaretskaya & S. N. Ananchenko

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  1. I. N. Nazarov
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  2. G. P. Verkholetova
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  3. I. V. Torgov
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  4. I. I. Zaretskaya
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  5. S. N. Ananchenko
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Nazarov, I.N., Verkholetova, G.P., Torgov, I.V. et al. Synthesis of steroid compounds and related substances Communication XX. Condensation of 3,4,4a,7,8,8a-hexahydro-4a-methyl-5-vinyl-2(1H)-naphthalenone and 3,4,4a,5,6,8a-hexahydro-8a-methyl-8-vinyl-2(1H)-naphthalenone with 2-cyclopenten-i-one, 2-methyl-2-cyclopenten-1-one, and 3,5-dimethyl-9-cyclopentene-1,2-dione. Russ Chem Bull 2, 827–836 (1953). https://doi.org/10.1007/BF01178861

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  • DOI: https://doi.org/10.1007/BF01178861

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