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Synthesis of steroid compounds and related substances Communication XIX. 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-cyclohexen-1-ones and with citraconic anhydride

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

Summary

  1. 1.

    The total syntheses of some D-homosteroid diketones of the cis-cis series having a 15-keto group have been effected by condensation of 3,4,4a,7,8,8a-hexahydro-4a-methyl-5-vinyl-2(1H)-naphthalenone (I) with 2-methyl-2-cyclohexen-1-one (III). Four isomeric tetracyclic ketones have been isolated, and of these two, VI A and VI C, differ only in the spatial disposition of the hydrogen at C8, the third; VI D, differs in the position of the double bond (8- instead of 9-), and the fourth (VI B) differs from the other three in the spatial arrangement of the substituents at C13-C14

  2. 2.

    It has been shown that in the course of the diene condensation the double bond may be displaced from the 9(11)- to the 8(9)-position.

  3. 3.

    When the steroid diketones are subjected to Clemmensen reduction, only the keto group in the ring A is removed. and the diketone is converted into a 15-monoketone.

  4. 4.

    Condensation of 3,4,4a,5,6,8a-hexahydro-8a-methyl-8-vinyl-2(1H)-naphthalenosne (II) with 2 methyl 2-cyclohexen-1-one (III) yielded three isomeric steroid diketones, IX A, IX B, and IX C. Condensations of 3,4,4a, 7,8,8a hexahydro-4a-methyl-5-vinyl-2(1H)-naphthalenone (I) with 2-cyclohexen-1-one, p-benzoquinone, and citraconic anhydride have also been carried out, and the compounds X, XI, and XII haye been obtained.

  5. 5.

    Reduction of 3,4,4a,7,8,8a hexahydro-4a-methyl-5-vinyl-2(1H)-naphthalenone (I) with aluminum isopropoxide yielded 1,2,3,4,4a,7,8,8a-octahydro-4a-methyl-5-vinyl-2-naphthol (XIII), which, on being condensed with p-benzoquinone, yielded the tetracyclic hydroxy diketone XIV.

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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, I. I. Zaretskaya, G. P. Verkholetova & I. V. Torgov

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  1. I. N. Nazarov
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  2. I. I. Zaretskaya
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  3. G. P. Verkholetova
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  4. I. V. Torgov
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Nazarov, I.N., Zaretskaya, I.I., Verkholetova, G.P. et al. Synthesis of steroid compounds and related substances Communication XIX. 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-cyclohexen-1-ones and with citraconic anhydride. Russ Chem Bull 2, 817–825 (1953). https://doi.org/10.1007/BF01178860

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  • DOI: https://doi.org/10.1007/BF01178860

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