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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2023 Volume 33, Issue 4, Pages 479–480 (Mi mendc433)

This article is cited in 1 paper

Communications

A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester

Z. R. Makaev, N. S. Vostrikov, N. K. Selezneva, M. S. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

Abstract: A simple and facile synthesis of racemic 15-deoxy-Δ12,14-prostaglandin J2 methyl ester from readily available Corey lactone diol in total eleven steps was suggested. The standard methods provided a pathway to a block with an integrated w w w-chain and further to PGJ2 methyl ester. The latter was smoothly converted to the target prostaglandin in the TsOH–CH2Cl2 medium when allylic alcohol moiety was transformed to exocyclic diene substituent conjugated with endocyclic enone system.

Keywords: Corey lactone diol, prostaglandin J2 methyl ester, 15-deoxyΔ12,14-prostaglandin J2, diastereoselective reaction, dehydration, dienes.

Language: English

DOI: 10.1016/j.mencom.2023.06.012



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