Biomedical Engineering Reference
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H
N
O
O
N
O
MeO
N
H
Cl
OH
Cl
OMe
O
O
N
H
OH
OMe
OH
Rebeccamcine
Asterriquinone B1
O
MeO
Br
O
O
11
O
MeO
Br
O
O
Br
N
OMe
13
TIPS
O
C
8
F
17
OMe
Pd(PPh
3
)
4
Tl
2
CO
3
, PhH, 80°C
100%
N
SO
2
1. Pd(PPh
3
)
4
Tl
2
CO
3
, PhH, 80°C
2. CsF, THF/MeOH (1:1)
O
N
BsRf
10
12
C
8
F
17
88%
Me
N
N
O
O
1. MeI, Cs
2
CO
3
MeO
MeO
DMF
2. Mg, NH
4
Cl
THF/MeOH (1:1)
OMe
OMe
O
O
N
N
H
91%
14
15
BsRf
Other dihalo-substituted central rings
C
8
F
17
O
S
O
MeO
N
Cl
SO
2
Cl
Cl
S
Cl
N
Cl
Cl
N
Cl
Cl
C
8
F
17
BsRf
SCHEME 10.3
Fluorous sulfonyl linker (BsRf)-facilitated synthesis of bis-indoles.
the
cis
-hexahydroindeno[2,1-
b
]indol-6-one derivative
18
. This compound was
stereoselectively reduced to the corresponding alcohol using diisobutylaluminum
hydride (DIBAL-H) and then condensed with indole to give compound
19
. The
fluorous linker was finally removed by treatment with TBAF to afford yuehchukene.
H
1. MesLi, Et
2
O
-40°C
2.
C
8
F
17
1. IBX, DMSO
2. BF
3
.
OEt
2
PhH, 80°C
F-SPE
N
S
N
H
O
N
OH
O
O
BsRf
BsRf
OHC
C
8
F
17
-78°C to 0°C
16
17
18
50%
F-SPE, 67%
C
8
F
17
TBAF
Dioxane, 80°
C
H
H
1. DIBAL-H
THF, 0°C
2. Indole
BF
3
.
OEt
2
Et
2
O, 0°C
F-SPE
SO
2
F-SPE
N
H
N
H
H
C
8
F
17
BsRf
55%
BsRf
H
H
19
Yuehchukene
99%
SCHEME 10.4
Fluorous sulfonyl linker (BsRf)-facilitated synthesis of yuehchukene.
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