Propose an efficient synthesis for the following transformation The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. D. A B C HBr HBr, ROOR NazCr,07, H,SO4. H;0 t-BUOK H. F H2, Lindlar's cat. 1) O: 2) DMS TSCI, py dilute H,SO4 K 1) LIAIH4: 2) H,O DMP or PCC conc. H,SO4. heat 1) MeMgBr: 2) H,O eTextbook and Media

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 20.54P
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Propose an efficient synthesis for the following transformation
of
The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary
reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct
solution, provide just one answer.
D
A
B
HBr
t-BUOK
HBr, ROOR
NazCr,07, H,SO4. H20
E
F
H2, Lindlar's cat.
1) O3: 2) DMS
TSCI, py
dilute H,SO4
K
conc. H,SO4. heat
1) MeMgBr: 2) H3O*
1) LIAIH4: 2) H3O
DMP or PCC
eTextbook and Media
Transcribed Image Text:Propose an efficient synthesis for the following transformation of The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. D A B HBr t-BUOK HBr, ROOR NazCr,07, H,SO4. H20 E F H2, Lindlar's cat. 1) O3: 2) DMS TSCI, py dilute H,SO4 K conc. H,SO4. heat 1) MeMgBr: 2) H3O* 1) LIAIH4: 2) H3O DMP or PCC eTextbook and Media
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