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
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 19.67P
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Question
Propose a mechanism for the conversion of D to E
![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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fdc71590e-ac89-4919-8241-33245756139d%2Fe225c7c8-b9f0-46d2-85a4-9d9a1de6f492%2Fyxy1e7j.jpeg&w=3840&q=75)
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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fdc71590e-ac89-4919-8241-33245756139d%2Fe225c7c8-b9f0-46d2-85a4-9d9a1de6f492%2F40bvfo.jpeg&w=3840&q=75)
Transcribed Image Text:0-THP
0-THP
HO
Ho+
ОН
OH
BnO
НО
C
D
Cl.
NMeg
HCI
F
Toremifene
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