OPTICALLY-ACTIVE TRANS-DIETHYLSTILBESTROL OXIDE MONOMETHYL ETHER

Diethylstilbestrol oxide is a metabolic intermediate of diethylstilbes trol. In order to elucidate the effects of optically active diethylsti lbestrol oxides on microtubule assembly and cell culture, we synthesiz ed (+/-)-diethylstilbestrol oxide (2a). Since 2a was not stable under moderately acidic and basic conditions, the monomethyl ether (2c) of d iethylstilbestrol oxide, which was more stable than 2a, was separated by high-pressure liquid chromatography using a chiral column. The mono (4-bromobenzoate) of (-)-2c was analyzed by X-ray crystallography and its absolute structure was determined as C (IR,1'R).