Estrogens are female sex hormones, the most potent of which is
\(\beta\)-estradiol.
In recent years, chemists have focused on designing and synthesizing molecules
that bind to estrogen receptors. One target of this research has been
nonsteroidal estrogen antagonists, compounds that interact with estrogen
receptors and block the effects of both endogenous and exogenous estrogens. A
feature common to one type of nonsteroidal estrogen antagonist is the presence
of a 1,2 -diphenylethylene with one of the benzene rings bearing a
dialkylaminoethoxyl substituent. The first nonsteroidal estrogen antagonist of
this type to achieve clinical importance was tamoxifen, now an important drug
in the treatment of breast cancer. Tamoxifen has the \(Z\) configuration as
shown here.
Propose reagents for the conversion of A to tamoxifen. Note: The final step in
this synthesis gives a mixture of \(E\) and \(Z\) isomers.