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Synthesis of 19-morsteroids based on 3-methoxy-d-homoestra-1,3,5(10),8,14-pentaen-17a-one

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Summary

  1. 1.

    By the reduction of 3-methoxy-D-homoestra-1,3,5(10),8-tetraen-17a-one (III) with lithium and alcohol in liquid ammonia with subsequent hydrolysis, 19-nor-D-homoandrost-4-en-3,17a-dione (V) was obtained. A similar reduction of the ethylene ketal of 3-methoxy-D-homoestra-1,3,5(10),8,14-pentaen-17a-one (I) with a large excess of lithium led to 19-nor-D-homoandrosta-4,8-dien-3,17a-dione (XIII). Reduction of the ketal of (I) in the absence of alcohol gave ketal (III).

  2. 2.

    In acid medium 3-methoxy-D-homoestra-1,3,5(10),8-tetraen-17a-one (II) and its ketal (III) were partially dehydrogenated to the methyl ether of trans-D-homoequilenin (VII) or its ketal (VI); at the same time products were formed with a double bond in a different position than in ketone (I).

  3. 3.

    Under the conditions of demethylation 3-methoxy-D-homoestra-1.3,5(10),8,14-pentaen-17a-one (I) and 3-methoxy-8,14-seco-D-homoestra-1,3,5(1'0),9-tetraen-14,17a-dione (X) formed trans-D-homoequilenin (IX). Thus, starting from 6-methoxytetralone the synthesis of trans-D-homoequllenin was carried out in a total of three steps.

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Literature cited

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Ananchenko, S.N., Platonova, A.V., Leonov, V.N. et al. Synthesis of 19-morsteroids based on 3-methoxy-d-homoestra-1,3,5(10),8,14-pentaen-17a-one. Russ Chem Bull 10, 993–998 (1961). https://doi.org/10.1007/BF00909174

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Keywords

  • Alcohol
  • Methyl
  • Ether
  • Ammonia
  • Hydrolysis