Biomedical Engineering Reference
In-Depth Information
R
2
R
2
R
3
Br
R
3
CuI,
L7
, K
2
CO
3
PhMe, 120°C
Br
NCbz
R
4
NH
N
R
4
R
5
NHCbz
R
1
56-84%
R
5
O
O
R
1
76
77
(ee = 6-93%)
R
1
= Me, H, Bn, iPr, CH
2
CH(Me)
2
, CH
2
CH
2
OBn, (CH
2
)
3
CH
2
NHBoc
R
2
= H, Me, OBn R
3
= H, OBn, OMe R
4
= H, OBn, CF
3
, F R
5
= H, OMe
Me
O
N
NH
N
O
N
O
HN
N
OH
HO
H
H
NH
Me
NH
Me
N
N
Me
Me
O
O
Asperlicin
Fumiquinazoline I
SCHEME 3.29
Synthesis of substituted imidazoindolones by Lautens and coworkers.
The group of Evano significantly contributed to the total synthesis of cyclopep-
tide alkaloids via copper-assisted macrocyclization by enamide bond formation since
2006 [78]. The copper-catalyzed macrocyclization that allowed to install the enamide
moiety in a single step compared favorably with the tedious procedures reported so
NH
2
NH
X
HO
2
C
O
HN
NMe
t
BuO
2
C
N
Me
O
O
6 steps
CuI, K
2
CO
3
DMF, 90°C
t
BuO
2
C
Me
CO
2
H
H
NH
2
I
HO
2
C
N
O
78
79
HClH
ξ
N
SB-214857
NHMe
N
10 steps
CuI, K
3
PO
4
DMSO, 80°C
91%
N
N
NBoc
N
H
N
Me
H
N
N
N
Boc
NH
Br
80
81
NHMe
(
±
)-Psychotrimine
SCHEME 3.30
Total syntheses of SB-214857 and (
)-psychotrimine.
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