4. (a) Consider the reaction scheme below: OH Ph HO -OEt HO OEt HO Step 1 HO AcO- (i) Provide reagents for BOTH Step 1 and Step 3. (ii) Provide a curved arrow mechanism for Step 1. HO Step 2 Ph AcO- BnO Aco -OEt Step 3 OH Aco OEt

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
Section20.6: Sigmatropic Shifts
Problem 20.12P
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4
4.
(a) Consider the reaction scheme below:
OH
HO
-0
-OEt
HO
-OEt
HO
Step 1
HO
-0
ACO
ACO
(i) Provide reagents for BOTH Step 1 and Step 3.
(ii) Provide a curved arrow mechanism for Step 1.
(b) Provide a curved arrow mechanism for the following reaction and
explain the stereochemical outcome.
OH
BzO
Bz0
OBz
OBZ
Bz0
BZO SEt
HO
BZ0-
820
OMe
TIOH
CH₂Cl₂
4 A molecular sieves
BzO
Bz0
Step 2
BzO
Ph
0-
Aco
BnO
B20-
BZO
ACO
OH
-OEt
Step 3
Bzoome
-OEt
Transcribed Image Text:4. (a) Consider the reaction scheme below: OH HO -0 -OEt HO -OEt HO Step 1 HO -0 ACO ACO (i) Provide reagents for BOTH Step 1 and Step 3. (ii) Provide a curved arrow mechanism for Step 1. (b) Provide a curved arrow mechanism for the following reaction and explain the stereochemical outcome. OH BzO Bz0 OBz OBZ Bz0 BZO SEt HO BZ0- 820 OMe TIOH CH₂Cl₂ 4 A molecular sieves BzO Bz0 Step 2 BzO Ph 0- Aco BnO B20- BZO ACO OH -OEt Step 3 Bzoome -OEt
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