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t BuO 2 C
O
O
H
t BuO 2 C
CO 2 t Bu
Barton's base ( 5 )
O
B
CD
O
O
O
76%
H
OO
5.9 : 1
CO 2 t Bu
Me
Me
Me
Me
35
36
2. AcOH, H 2 O
air, 70%
1. KOH, BnBr, 78%
O
Me
O
N
O
OH
t BuO 2 C
O
F
A
O
OH
MeO
1. RuCl 3 , NaIO 4
64%
O
O
O
A
BnO 2 C
BnO 2 C
B
O
C
DE
B
O
C
D
O
OH
2. TFA
26%
O
O
HO
O
O
O
Me
38
37
lactonamycin ( 39 )
OH
Scheme 7.6
Synthesis of A-D ring system for lactonamycin (39)
 
 
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