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Transformed steroids

Communication 44. Synthesis of acetonides of Δ4-21-homopregnene-16α, 17α, 21ξ, 21a-tetrol-3, 20-dione

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

Conclusions

  1. 1.

    The opening of the 16α, 17α-epoxypregnenolone acetate in the presence of carboethoxyhydrazine, followed by condensation with acetone and subsequent condensation with formaldehyde, gave the stereoisomeric 16α, 17α-isopropylidenedioxy-Δ4-21-homopregnene-21ξ, 21a-diol-3, 20-diones, which were then converted to the 16α,17α∶21ξ, 21a-isopropylidenedioxy-Δ4-21-homopregnene-3, 20-diones, to which was assigned the R- and S-configuration at C-21 on the basis of studying the reaction of the 16, 17-monoacetonides of the tetrols with the anhydride of racemicα-phenylbutyric acid and the results of studying the circular dichroism of the C-21 epimeric alcohols.

  2. 2.

    The predominant formation of the R-isomer of 16α, 17α-isopropylidenedioxy-Δ4-21-homopregnene-21, 21a-3, 20-dione is observed when condensation is with formaldehyde.

  3. 3.

    The treatment of the 16α, 17α, 21ξ, 21a-diisopropylidene derivatives with acetic acid causes the removal of the protection of only the 21ξ, 21a-hydroxyl groups.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    A. A. Akhrem, A. V. Kamernitskii & I. G. Reshetova

Authors
  1. A. A. Akhrem
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  2. A. V. Kamernitskii
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  3. I. G. Reshetova
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Additional information

See [1] for Communication 43.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1364–1368, June, 1972.

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Akhrem, A.A., Kamernitskii, A.V. & Reshetova, I.G. Transformed steroids. Russ Chem Bull 21, 1313–1316 (1972). https://doi.org/10.1007/BF00854551

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  • DOI: https://doi.org/10.1007/BF00854551

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