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Transformed steroids Communication 57. Use of the mannich reaction to build up the side chain of steroids

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

Conclusions

  1. 1.

    A steroidal divinyl ketone, namely 21-homopregna-5,16,21-trien-3β-ol-20-one 3-acetate (III), the starting product in the synthesis of polyhydroxy steroids, was synthesized in 64% yield by starting with the readily-available dehydropregnenolone acetate via the Mannich reaction and subsequent cleavage.

  2. 2.

    A siudy was made of the reactivity of the conjugated bonds in divinyl ketone (III) under the conditions of hydration and the addition of alcohols in acid and alkaline media.

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Literature cited

  1. A. A. Akhrem, A. V. Kamernitskii, and I. G. Reshetova, Izv. Akad. Nauk SSSR, Ser. Khim., 1128 (1973).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1633–1637, July, 1973.

See [1] for Communication 56.

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Akhrem, A.A., Kamernitskii, A.V., Reshetova, I.G. et al. Transformed steroids Communication 57. Use of the mannich reaction to build up the side chain of steroids. Russ Chem Bull 22, 1578–1582 (1973). https://doi.org/10.1007/BF00930066

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  • DOI: https://doi.org/10.1007/BF00930066

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