3. The following reaction is used in the industrial synthesis of the antiviral drug, oseltamivir (Tamiflu), by the pharmaceutical company, Roche. Propose a mechanism for this transformation. OEt Hint: first, the acetal is hydrolyzed using water and triflic acid (a very strong acid), then the resulting diol can form an acetal with pentan-3-one. NH,-H,PO, oseltamivir OEt OEt TIOH ÕMs H20 OMs TIOH = F,c-s-OH triflic acid

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
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.47P
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3. The following reaction is used in the industrial synthesis of the antiviral drug, oseltamivir (Tamiflu), by the pharmaceutical company, Roche. Propose a mechanism for this transformation.

3. The following reaction is used in the industrial synthesis of the antiviral drug,
oseltamivir (Tamiflu), by the pharmaceutical company, Roche. Propose a
mechanism for this transformation.
OEt
Hint: first, the acetal is hydrolyzed using water and triflic acid (a very strong acid),
then the resulting diol can form an acetal with pentan-3-one.
NH,-H,PO,
oseltamivir
OEt
OEt
TFOH
H20
ÖMs
OMs
TFOH =
F,C-S-OH
triflic acid
Transcribed Image Text:3. The following reaction is used in the industrial synthesis of the antiviral drug, oseltamivir (Tamiflu), by the pharmaceutical company, Roche. Propose a mechanism for this transformation. OEt Hint: first, the acetal is hydrolyzed using water and triflic acid (a very strong acid), then the resulting diol can form an acetal with pentan-3-one. NH,-H,PO, oseltamivir OEt OEt TFOH H20 ÖMs OMs TFOH = F,C-S-OH triflic acid
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