Eistrogens are female sex hormones, the most potent of which is B-estradiol. OH H,C но B-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 nonste- roidal 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 shown here. но NMe, NMeg ? B NMeg ? "NMe, ОН Tamoxifen Propose reagents for the conversion of A to tamoxifen. Note: The final step in this synthesis gives a mixture of E and Z isomers.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.63P
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Eistrogens are female sex hormones, the most potent of which is B-estradiol.
OH
H,C
но
B-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 nonste-
roidal 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 shown here.
но
NMe,
NMeg ?
B
NMeg ?
"NMe,
ОН
Tamoxifen
Propose reagents for the conversion of A to tamoxifen. Note: The final step in this
synthesis gives a mixture of E and Z isomers.
Transcribed Image Text:Eistrogens are female sex hormones, the most potent of which is B-estradiol. OH H,C но B-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 nonste- roidal 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 shown here. но NMe, NMeg ? B NMeg ? "NMe, ОН Tamoxifen Propose reagents for the conversion of A to tamoxifen. Note: The final step in this synthesis gives a mixture of E and Z isomers.
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