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Synthesis of 13,14-Dehydro-15-deoxy-16-hydroxy-16-methyl-17-phenoxyprostaglandin B1 Ethyl Ester

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Abstract

A new synthetic route has been developed for the construction of the main skeleton of ω-aryloxyprostaglandin (PG) via 1,2-addition of lithiated 3-methyl-3-(trimethylsilyloxy)pent-1-yne to the ketone carbonyl group of ethyl 7-(5-oxocyclopent-1-en-1-yl)heptanoate. The addition reaction was accompanied by the formation of cyclopentenone dimer as minor product. The 1,2-adduct containing a tertiary hydroxy group was oxidized with pyridinium chlorochromate to 13-dehydro-PGB1 ethyl ester.

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ACKNOWLEDGMENTS

The spectral and analytical data were obtained using the equipment 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. AAAA-A20-120012090021-4.

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Authors and Affiliations

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

    N. A. Ivanova, G. A. Shavaleeva & M. S. Miftakhov

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  1. N. A. Ivanova
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  2. G. A. Shavaleeva
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  3. M. S. Miftakhov
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Corresponding author

Correspondence to N. A. Ivanova.

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The authors declare the absence of conflict of interest.

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Ivanova, N.A., Shavaleeva, G.A. & Miftakhov, M.S. Synthesis of 13,14-Dehydro-15-deoxy-16-hydroxy-16-methyl-17-phenoxyprostaglandin B1 Ethyl Ester. Russ J Org Chem 56, 540–543 (2020). https://doi.org/10.1134/S1070428020030288

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  • DOI: https://doi.org/10.1134/S1070428020030288

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