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Synthesis of (±)-D-homoestrone, (±)-8-iso-D-homoestrone, and the corresponding estradiols

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

Summary

  1. 1.

    By the selective and exhaustive hydrogenation of (±)-8,14-didehydro-D-homoestrone (I) we obtained (±)-8-dehydro-D-homoestrone (II) and (±)-8-iso-D-homoestrone (III), respectively. By the reduction of (±)-8-dehydeo-D-homoestrone 3-(tetrahydropyran-2yl) ether (IV) with potassium in liquid ammonia with subsequent hydrolysis we synthesized (±)-D-homoestrone (VI). (±)-D-Homoestrone (VI) was also prepared in good yield by the demethylation of (±)-D-homoestrone 3-methyl ether (VII).

  2. 2.

    The reduction of the ketones (I), (II), (III), and (VI) with lithium aluminum hydride led stereospecifically and in high yields to the corresponding 17α,β-hydroxy compounds.

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Literature cited

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Authors and Affiliations

  1. Institute for the Chemistry of Natural Products, Academy of Sciences, USSR

    V. E. Limanov, S. N. Ananchenko & I. V. Torgov

Authors
  1. V. E. Limanov
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  2. S. N. Ananchenko
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  3. I. V. Torgov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seria Khimicheskaya, No. 10, pp. 1814–1819, October, 1964

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Limanov, V.E., Ananchenko, S.N. & Torgov, I.V. Synthesis of (±)-D-homoestrone, (±)-8-iso-D-homoestrone, and the corresponding estradiols. Russ Chem Bull 13, 1720–1724 (1964). https://doi.org/10.1007/BF00849435

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  • DOI: https://doi.org/10.1007/BF00849435

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