Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose struc- ture is closely related to that of tamoxifen. 1. THP-O -Br, Mg 1. E:ONA 2. BICH,CH,OBn 2. H,O, HCI BnO A B 0-THP 0-THP HO Ho+ ОН OH BnO НО C D Cl. NMeg HCI F Toremifene

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
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.68P
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Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?

Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose struc-
ture is closely related to that of tamoxifen.
1. THP-O
-Br, Mg
1. E:ONA
2. BICH,CH,OBn
2. H,O, HCI
BnO
A
B
Transcribed Image Text:Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose struc- ture is closely related to that of tamoxifen. 1. THP-O -Br, Mg 1. E:ONA 2. BICH,CH,OBn 2. H,O, HCI BnO A B
0-THP
0-THP
HO
Ho+
ОН
OH
BnO
НО
C
D
Cl.
NMeg
HCI
F
Toremifene
Transcribed Image Text:0-THP 0-THP HO Ho+ ОН OH BnO НО C D Cl. NMeg HCI F Toremifene
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