Large-scale synthesis of the catechol metabolites of diethylstilbestrol and hexestrol

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Abstract

Diethylstilbestrol (DES) and hexestrol (HES) are carcinogenic synthetic estrogens. The major metabolites of these compounds are their catechol derivatives, 3'-OH-DES and 3'-OH-HES. Oxidation of these metabolites leads to the electrophilic quinones, which are presumably involved in the tumor- initiating process. A synthetic route based on the McMurry coupling reaction was developed for the synthesis of 3'-OH-DES. Using commercially inexpensive starting materials, this compound was synthesized in four steps, and the cis and trans isomers were separated and identified. Following the same synthetic route, 3'-OH-HES was synthesized in five steps.

Original languageEnglish (US)
Pages (from-to)408-411
Number of pages4
JournalChemical Research in Toxicology
Volume11
Issue number5
DOIs
Publication statusPublished - Jun 8 1998

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ASJC Scopus subject areas

  • Toxicology

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