A versatile synthesis of 2-methoxyestradiol, an endogenous metabolite of estradiol which inhibits tubulin polymerization by binding to the colchicine binding site

Abstract

A versatile synthesis of 2-methoxyestradiol ( 7) is described. Formylation of estradiol ( 1) with hexamethylenetetramine gave 2-formylestradiol ( 3). Benzylation of the two hydroxyl groups of 3 under basic conditions with benzyl bromide afforded the dibenzyl ether 4. 2-Methoxyestradiol ( 7) was then obtained from 4 by Baeyer-Villiger oxidation, methylation of the phenol, and debenzylaion.