Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen
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Updated: Oct 5, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
M Teranishi1, M Kashihara, Y Fujii
1Faculty of Pharmaceutical Sciences, Hokuriku University, Ho-3, Kanagawa-machi, 920-1181, Kanazawa, Japan. m-teranishi@hokuriku-u.ac.jp
Abstract:
The introduction of an oxygen atom into the C-6 position of 4-hydroxyestrogen allowed for the selective methylation of the two phenolic hydroxyl groups. When the 6-oxo derivative of 4-hydroxyestrone was benzylated in ethanol, only the 3-monobenzyl ether was obtained without formation of the 4-monobenzyl ether. Moreover, the 6-carbonyl group was further reduced to methylene almost quantitatively in the reaction of 4-acetoxy-6-oxoestrone 3-benzyl ether derivative with sodium borohydride. Therefore, 4-methoxyestrogen was synthesized by essentially combining these two reactions.
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