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Transformed steroids. 193. Synthesis of 16α,17α-isopropylidene derivatives of pregn-4-ene-9α,16α,17α,21-tetraol-3,20-dione and its 17α-thioanalog

  • Chemistry Of Natural Products
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Bulletin of the Russian Academy of Sciences, Division of chemical science Aims and scope

Abstract

A study was carried out on the pathways for the transformation of 16α,17α-epoxypregn-4-ene-9α,21-diol-3,20-dione to give 16α,17α-isopropylidene derivatives of pregn-4-ene-9α,16α,17α,21-tetraol-3,20-dione and its 17α-thioanalog. The key step in this pathway is thecis-cleavage of the 20-carboethoxyhydrazone of this epoxide by acetic and thioacetic acids and subsequent condensation of the products formed with acetone. This pathway is an efficient approach to the synthesis of the 16α,17α-dioxolane derivative and is equally efficient for preparation of the thioanalog, namely, 16α,17α-isopropylidenepregn-4-ene-9α,16α,21-triol-17α-thiol-3,20-dione, which has already been synthesized by an alternative method.

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Authors
  1. A. M. Turuta
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  2. A. V. Kamernitskii
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  3. N. V. Dzhlantiashvili
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  4. A. A. Korobov
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  5. N. E. Voishvillo
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Additional information

For previous communication, see [1].

N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 10, pp. 2436–2440, October, 1992.

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Turuta, A.M., Kamernitskii, A.V., Dzhlantiashvili, N.V. et al. Transformed steroids. 193. Synthesis of 16α,17α-isopropylidene derivatives of pregn-4-ene-9α,16α,17α,21-tetraol-3,20-dione and its 17α-thioanalog. Russ Chem Bull 41, 1916–1919 (1992). https://doi.org/10.1007/BF00863832

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  • DOI: https://doi.org/10.1007/BF00863832

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