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. A t-BuOK B C D HBr, ROOR Na2Cr2O7, H2SO4, H2O HBr E F G H H2, Lindlar's cat. 1) O3; 2) DMS TsCl, py dilute H2SO4 I J K L 1) LiAlH4; 2) H3O+ DMP or PCC conc. H2SO4, heat 1) MeMgBr; 2) H3O+

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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.
A
t-BuOK
B
C
D
HBr, ROOR
Na2Cr2O7, H2SO4, H2O
HBr
E
F
G
H
H2, Lindlar's cat.
1) O3; 2) DMS
TsCl, py
dilute H2SO4
I
J
K
L
1) LiAlH4; 2) H3O+
DMP or PCC
conc. H2SO4, heat
1) MeMgBr; 2) H3O+
Transcribed Image Text: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. A t-BuOK B C D HBr, ROOR Na2Cr2O7, H2SO4, H2O HBr E F G H H2, Lindlar's cat. 1) O3; 2) DMS TsCl, py dilute H2SO4 I J K L 1) LiAlH4; 2) H3O+ DMP or PCC conc. H2SO4, heat 1) MeMgBr; 2) H3O+
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