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.
journal_name
Chem Res Toxicoljournal_title
Chemical research in toxicologyauthors
Jan ST,Rogan EG,Cavalieri ELdoi
10.1021/tx970140vsubject
Has Abstractpub_date
1998-05-01 00:00:00pages
408-11issue
5eissn
0893-228Xissn
1520-5010pii
tx970140vjournal_volume
11pub_type
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