Biomedical Engineering Reference
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O
OMe
OMe
O
O
O
O
PhH, 120°C
sealed tube
H
I
B O
O
OMe
O
O
O
OMe
94
97
100
( rac )- 104
(15%)
O
H
PdCl 2 (MeCN) 2
DMF, 50°C
darkness
O
OMe
( rac )- 105
(6%)
O
B
O
O
OMe
O
O
95
O
Pd(PPh 3 ) 4 , THF
aq KOH, 80°C
Xylene, 150°C
darkness
H
H
O
OMe
OH
O
O
O
OMe
OMe
101
( rac )- 103
(4%)
( rac )- 104
(10%)
( rac )- 106
(9%)
Br
O
OMe
98
OMe
OMe
Cyclohexane
h
O
O
, rt
ν
H
( rac )- 107
(9%)
O
O
( rac )- 108
(4%)
O 2 , CHCl 3 , methylene blue, h
ν,
rt
O
O
O
O
O
O
Pd(PPh 3 ) 4 , THF
aq KOH, 80°C
Br
MeOH, h
ν,
rt
MeOH, h
ν,
rt
B O
O
O
O
OMe
O
OMe
O
OMe
OMe
( rac )- 109
(25%)
O
O
OMe
96
99
102
( rac )- 110
(18%)
( rac )- 111
(99% conversion)
 
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