Biomedical Engineering Reference
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O
NO
2
NO
2
OMe
R
E
Pd(CH
3
CN)
2
Cl
2
DMF, rt
H
O
R
Z
+
O
53%
H
H
I
334
335
336
Me
3
Sn
O
2
N
O
O
6
R
E
16
8
10
endo
H
O
H
H
OMe
15
H
Ar
R
Z
337
SNF4435 C
339
+ diastereomer
O
2
N
O
exo
O
Ar
R
Z
H
O
H
OMe
R
E
H
H
338
SNF4435 D
340
SCHEME 9.58
Parker and Lim's synthesis of SNF4435 C (
339
).
Br
SnBu
3
Pd(PPh
3
)
4
Toluene,
CO
2
Me
CO
2
Me
Δ
TBDPSO
N
( )
5
TBDPSO
N
( )
5
NBoc
68%
NBoc
O
O
OTBDPS
341
342
OTBDPS
N
CO
2
Me
H
H
H
steps
H
A
B
OH
TBDPSO
N
N
( )
5
C
D
H
NBoc
O
N
OTBDPS
E
343
Manzamine A
344
SCHEME 9.59
Synthesis of manzamine A
344
by Martin and coworkers.
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