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Key structures for the synthesis of steroid antitumor agents. Synthesis of 16-dehydro-17-carbaldehydes of 13β- and 13α-estratriene series

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Abstract

A convenient preparative synthesis of 3-methoxyestra-1,3,5(10),16-tetraene-17-carb-aldehyde and its epimeric 13α-analog, the key structures in the synthesis of steroid estrogen receptor modulators and potential antitumor agents, was developed starting from estrone and including the generation of intermediate 16-dehydro-17-carbonitriles and their reaction with diisobutylaluminum hydride. The influence of conformational dif erences in the steroid molecules with the natural 13β- and epimeric 13α-configurations on the reactivity of intermediate compounds and the stereoselectivity of the trimethylsilyl cyanide addition to the carbonyl group of methyl ethers of epimeric estrones was considered.

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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, I. S. Levina & I. V. Zavarzin

Authors
  1. M. O. Tserfas
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  2. Yu. V. Kuznetsov
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  3. I. S. Levina
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  4. I. V. Zavarzin
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Corresponding author

Correspondence to Yu. V. Kuznetsov.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (Project No. 19-03-00-246).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2350–2354, December, 2019.

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Tserfas, M.O., Kuznetsov, Y.V., Levina, I.S. et al. Key structures for the synthesis of steroid antitumor agents. Synthesis of 16-dehydro-17-carbaldehydes of 13β- and 13α-estratriene series. Russ Chem Bull 68, 2350–2354 (2019). https://doi.org/10.1007/s11172-019-2710-1

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  • DOI: https://doi.org/10.1007/s11172-019-2710-1

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