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Key structures in the synthesis of steroid antitumor agents. Methods for upbuilding the 17β-pregnane side chain of 3-methoxy-19-norpregna-1,3,5(10)-trien-20-ones with and without an additional 16α,17α-carbocycle

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Abstract

Methods for extending the side chain of 20-oxopregnanes were summarized. The possibilities of alkylation of 3-methoxy-19-norpregna-1,3,5(10)-trien-20-one and its 16α,17α-methano and -butano derivatives with alkyl halides in the presence of lithium diisopropylamide were studied. The Claisen—Schmidt condensation of these steroids with aromatic aldehydes resulted in a series of the corresponding 21-benzylidenesteroids. Carrying out the Claisen—Schmidt condensation in an aprotic solvent in the presence of lithium diisopropylamide yielded, in addition to the target 21-benzylidenesteroids, the corresponding 21-benzoyl derivatives — steroidal 1,3-diketones.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. O. Tserfas, Yu. V. Kuznetsov, V. V. Knyazev, I. S. Levina & I. V. Zavarzin

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  1. M. O. Tserfas
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  2. Yu. V. Kuznetsov
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Corresponding author

Correspondence to Yu. V. Kuznetsov.

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Dedicated to the Academician of the Russian Academy of Sciences V. A. Tartakovsky on the occasion of his 90th birthday.

This work was financially supported by the Russian Science Foundation (Project No. 22-23-00778; u]https://rscf.ru/project/22-23-00778/).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1806–1817, August, 2022.

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Tserfas, M.O., Kuznetsov, Y.V., Knyazev, V.V. et al. Key structures in the synthesis of steroid antitumor agents. Methods for upbuilding the 17β-pregnane side chain of 3-methoxy-19-norpregna-1,3,5(10)-trien-20-ones with and without an additional 16α,17α-carbocycle. Russ Chem Bull 71, 1806–1817 (2022). https://doi.org/10.1007/s11172-022-3593-0

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