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Synthesis of (±)-Entecavir

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Abstract

A practical synthesis of (±)-entecavir has been developed on the basis of Corey (±)-lactone diol. The key stage is the synthesis of (1R*,3R*,4S*)-4-(1-ethoxyethoxy)-3-[(1-ethoxyethoxy)methyl]-2-methylidene­cyclo­pentan-1-ol by oxidative decarboxylation of 2-{(1S*,2R*,3S*,5R*)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-(1-ethoxyethoxy)-2-[(1-ethoxyethoxy)methyl]cyclopentyl}acetic acid with lead tetraacetate.

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Notes

  1. Hereinafter, signals of diastereoisomers are marked with an asterisk.

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ACKNOWLEDGMENTS

The spectral and analytical data were obtained using the facilities of the Chemistry joint center, Ufa Institute of Chemistry, Russian Academy of Sciences.

Funding

This study was performed in the framework of state assignment no. 122031400261-4 (Design and Synthesis of Bioactive Natural and Unnatural Cyclopentanoids, Hetero­cycles, Epothilones, and Their Analogues).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    Z. R. Valiullina, N. A. Ivanova & M. S. Miftakhov

Authors
  1. Z. R. Valiullina
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  2. N. A. Ivanova
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  3. M. S. Miftakhov
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Corresponding author

Correspondence to Z. R. Valiullina.

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The authors declare that they have no conflicts of interest.

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Valiullina, Z.R., Ivanova, N.A. & Miftakhov, M.S. Synthesis of (±)-Entecavir. Russ J Org Chem 60, 410–414 (2024). https://doi.org/10.1134/S1070428024030060

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  • DOI: https://doi.org/10.1134/S1070428024030060

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