Chemistry Reference
In-Depth Information
Pd(OAc)
2
(3 mol %)
(R)-
BINAP (9 mol %)
Ag
2
CO
3
(2 eq)
NMP, 60°C
CO
2
Me
CO
2
Me
(Shibasaki)
H
I
97
98
74%, 46% ee
Pd(OAc)
2
(10 mol %)
(R,R)
-DIOP (10 mol %)
Et
3
N
OTf
(Overman)
Benzene, rt
O
90%, 45% ee
O
100
99
Scheme 8C.38.
Pd(OAc)
2
(5 mol %)
(
R
)-BINAP (10 mol %
)
OH
CO
2
Me
CO
2
Me
O
O
K
2
CO
3
(2 eq)
KOAc (1 eq)
DCE, 60
o
C
H
TfO
O
H
102
70%, 86% ee
101
O
(+)-Vernolepin
103
OTBS
Me
Br
Pd(OAc)
2
(5 mol %)
(
R
)-BINAP (10 mol
%)
K
2
CO
3
(2 eq)
Benzene, 60°C
OTBS
-
H
OTf
H
Me
OH
105
63%, 73% ee
104
(-)-Oppositol
106
[Pd(allyl)Cl]
2
,
(S
)-BINAP
TBDPSO
CO
2
Et
CO
2
Et
Me
Me
EtO
2
C
H
H
OTf
O
TBD
PS
EtO
ONa
H
NaBr, DMSO, rt
Me
Me
(-)-Capnellene
109
108
77%, 87% ee
107
Scheme 8C.39.
polyketides such as halenaquinone, xestoquinone, and wortmannin [67,68]. Moreover,
the reaction has been employed as the key step in the synthesis of various alkaloids,
for example, physostigmine, quadrigemine C, spirotryprostatin B, and minfi ensine
[67,68] .
