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Practical F/Δ12,14-D transformation in the prostaglandin series. synthesis of methyl (±)-(5Z,12E,14E)-9α-acetoxy- 16-(3-chlorophenoxy)-15-deoxy-11-oxo-17,18,19,20-tetranorprosta- 5,12,14-trienoate from cloprostenol

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Abstract

Methyl (±)-(5Z,12E,14E)-9α-acetoxy-16-(3-chlorophenoxy)-15-deoxy-11-oxo-17,18,19,20-tetranorprosta- 5,12,14-trienoate was synthesized via selective protection/deprotection of the hydroxy groups in cloprostenol methyl ester, followed by oxidation of the C11–OH group and DBU-promoted elimination of the 9-acetoxy group.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    N. S. Vostrikov, I. F. Lobko, L. V. Spirikhin & M. S. Miftakhov

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  1. N. S. Vostrikov
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  2. I. F. Lobko
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  3. L. V. Spirikhin
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  4. M. S. Miftakhov
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Correspondence to M. S. Miftakhov.

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Original Russian Text © N.S. Vostrikov, I.F. Lobko, L.V. Spirikhin, M.S. Miftakhov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 12, pp. 1774–1781.

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Vostrikov, N.S., Lobko, I.F., Spirikhin, L.V. et al. Practical F/Δ12,14-D transformation in the prostaglandin series. synthesis of methyl (±)-(5Z,12E,14E)-9α-acetoxy- 16-(3-chlorophenoxy)-15-deoxy-11-oxo-17,18,19,20-tetranorprosta- 5,12,14-trienoate from cloprostenol. Russ J Org Chem 52, 1765–1772 (2016). https://doi.org/10.1134/S1070428016120095

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  • DOI: https://doi.org/10.1134/S1070428016120095

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