Biomedical Engineering Reference
In-Depth Information
O
O
H
H
O
CO
2
Et
CO
2
Et
Br
Br
CO
2
Et
H
H
HN
HN
Et
3
N, DMF
117
Br
119a
119c
CHO
ORf
8
h
3
ORf
8
h
3
μ
W (150°C, 20 min)
O
O
F-SPE
65%
O
O
O
H
H
Rf
8
h
3
O
(Rf
8
h
3
= C
8
F
17
CH
2
CH
2
CH
2
)
Br
CO
2
Et
Br
CO
2
Et
H
H
NH
2
118
HN
HN
119b
119d
ORf
8
h
3
ORf
8
h
3
O
O
O
CO
2
Et
H
H
p
-MeOC
6
H
4
NCO
K
2
CO
3
, DMF
100°C, 30 min
prep-LC
53%
Br
CO
2
Et
O
CH
2
Cl
2
, 25°C
O
H
N
N
O
N
F-SPE
85%
ORf
8
h
3
H
NH
O
O
OMe
Br
120a-120d
114
MeO
(8 detected, 6 isolated)
SCHEME 10.24
FDMS of hydantoin-fused hexahydrochromeno[4,3-
b
]pyrrole
114
.
CO
2
Et
CO
2
Et
CO
2
Et
CO
2
Et
H
H
H
H
O
O
O
O
O
O
O
O
N
N
N
N
N
N
N
H
H
H
H
O
O
O
O
OMe
OMe
OMe
OMe
Br
Br
Br
Br
114a
114a'
114b
114b'
cis-anti-trans
cis-syn-cis
trans-anti-cis
trans-syn-trans
(not isolated)
CO
2
Et
CO
2
Et
CO
2
Et
H
H
H
H
O
O
O
O
O
O
O
O
N
N
N
N
N
N
N
N
H
H
H
H
O
O
O
O
OMe
OMe
OMe
OMe
Br
Br
Br
Br
114c
cis-anti-cis
114c'
cis-syn-trans
114d
114d'
trans-anti-trans
trans-syn-cis
(not isolated)
FIGURE 10.5
Eight diastereomers of compounds
114
.
10.6. SUMMARY
Fluorous linker-facilitated synthesis integrates the characteristics of solution-phase
reactions and phase tag-based separations. Similar to conventional solution-phase
reactions, fluorous reactions have favorable reaction kinetics, broad synthetic scope,
and good compatibility with other synthetic, analytic, and separation technologies.
Fluorous solid-phase extraction simplifies the purification of reaction mixtures, and
fluorous HPLC is able to separate different components generated from the fluorous
mixture synthesis. The use of fluorous linkers for parallel and mixture syntheses
discussed in this chapter demonstrate the efficiency of this technology in the
preparation of natural product analogues and complex bioactive molecules.
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