Novel spiro-quinone formation from 3′-hydroxydiethylstilbestrol after oxidation with silver oxide

The human carcinogen diethylstilbestrol (DES) is metabolized into 3′-hydroxydiethylstilbestrol (3′-OH-DES) (1). Chemical oxidation of the catechol metabolites with silver oxide in CH2Cl2 affords a novel spiro-quinone (3) in quantitative yield. Protection of the phenolic OH group followed by oxidation gives 4″-OCH3-DES-3′,4′-Q (5) in excellent yield.