Biomedical Engineering Reference
In-Depth Information
O
O
O
Al
O
Li
(
S
)-ALB (
62
)
OHC
CO
2
Me
( )
OH
O
O
H
5
62
(10 mol%),
t-
BuONa (9 mol%)
MS 4Å, THF, rt
75%
CO
2
Me
( )
5
60
+
CO
2
Bn
CO
2
Bn
CO
2
Bn
TBSO
TBSO
CO
2
Bn
)
-
59
(
±
63
(12:1 mixture
of diastereomers)
61
TBSO
steps
Nu
O
Na
HO
O
CO
2
H
O
O
( )
5
Al
O
C
5
H
11
Li
THF
HO
OH
65
PGF
1
α
64
SCHEME 9.12
Synthesis of PGF
1
a
64
by Shibasaki and coworkers.
O
NH
H
N
OMe
O
CHO
N
72
(1 equiv)
O
+
H
O
MeO
HO
OMe
CH
2
Cl
2
/Toluene, -10°C
45%
CO
2
Me
N
66
67
68
HO
1. MsCl, Et
3
N, DMAP
CH
2
Cl
2
, 0°C to rt
2. NaOAc, HOAc, 120°C
46% (2 steps)
N
OMe
N
OMe
O
CO
2
Me
CO
2
Me
O
70
(64% ee)
69
steps
H
N
N
O
OH
NH
2
N
(-)-Cinchonidine
72
(-)-Huperzine A
71
SCHEME 9.13
Synthesis of huperzine A
71
by Terashima and coworkers.
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