Propose an efficient synthesis for the given transformation.
OH
OH
This transformation 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
B
C
D
E
$O$, $H_2SO_4$
1) $O$; 2)
$H_3O^+$
1) $O$; 2) $H_3O^+$
Mg
$H_2$, Lindlar's cat.
F
G
H
I
J
1) $HC \equiv CNa$; 2)
$H_3O^+$
$NaH$
$MCPBA$
$(RCO_3H)$
$Br_2$, hv
$HBr$ (xs), heat
K
L
M
N
O
$MeONa$
$DMP$ or $PCC$
$SOCl_2$, pyridine
$H_2SO_4$, $H_2O$,
$HgSO_4$
1) $R_2BH$; 2) $H_2O_2$,
$NaOH$
