Biomedical Engineering Reference
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OR
1
OR
1
OR
1
R
1
O
H
H
AuL
+
AuL
+
AuL
R
2
R
2
R
2
R
2
Ph
AuL
+
H
H
H
Ph
Ph
Ph
186
187
188
OR
1
Ph
AuL
+
+
R
2
190
189
OBn
MeO
[(JohnPhos)Au(NCCH
3
)]
+
SbF
6
-
(5 mol%)
BnO
O
OMe
O
O
O
O
CH
2
Cl
2
, rt, 2 h
O
O
Ph
O
79%
H
2
, Pd/C
93%
OMe
OH
O
O
OMe
OMe
O
O
O
O
N
O
O
Me
192
Macarpine
191
SCHEME 4.56
indoline
194
by the cycloisomerization of indole derivative
193
(Scheme 4.57) [54].
A subsequent methoxycarbonylation of
194
produced the new indoline
195
, which is
a known precursor of the alkaloid natural product minfiensine
. In a similar way,
Gagosz and coworkers developed a method that allowed the stereoselective
196
NHBoc
AuL
+
BocHN
AuL
(Ph
3
P)AuSbF
6
(5 mol
%
)
Toluene, 60°C, 2 h
N
H
Boc
H
H
87%
193
194
1.Triphosgene
Pyridine, CH
2
Cl
2
2. MeOH
80%
OH
N
N
N
Boc
MeO
2
C
MeO
2
C
195
196
Minfiensine
SCHEME 4.57
Synthesis of minfiensine by Wang and coworkers.
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