Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol

Paula S Kiuru; Kristiina Wähälä

doi:10.1016/s0039-128x(03)00035-7

Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol

Steroids. 2003 Apr;68(4):373-5. doi: 10.1016/s0039-128x(03)00035-7.

Authors

Paula S Kiuru¹, Kristiina Wähälä

Affiliation

¹ Department of Chemistry, Organic Chemistry Laboratory, University of Helsinki, A. I. Virtasen aukio 1, P.O. Box 55, FIN-00014 Helsinki, Finland.

PMID: 12787899
DOI: 10.1016/s0039-128x(03)00035-7

Abstract

The estrogen metabolite 2-methoxyestradiol was synthesized from estradiol bis-THP-ether which was 2-hydroxylated using the superbase LIDAKOR, trimethyl borate, and H(2)O(2), then methylated and deprotected to obtain 2-methoxyestradiol in three steps and 61% yield. 2-Hydroxyestradiol was obtained by deprotecting the 2-hydroxyestradiol bis-THP-ether from the first step.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

2-Methoxyestradiol
Estradiol / analogs & derivatives*
Estradiol / chemical synthesis*
Hydroxylation
Methylation

Substances

Estradiol
2-Methoxyestradiol
2-hydroxyestradiol