Chemistry Reference
In-Depth Information
1. LDA
CH
3
CHO
N
O
N
O
N
N
Boc
H
Boc
H
2. MsCl
Et
3
N
Me
105
104
OMs
THF, rt
DBN (
2
)
65%
(3 steps)
N
N
O
N
H
N
H
H
Boc
106
Me
Me
(+)-deplacheine (
107
)
Scheme 7.22
Synthesis of deplacheine (107)
Me
Me
Me
Me
Me
Me
Me
Me
O
Me
O
O
MTBD (
8
)
Me
H
Me
H
Me
H
DMF, 120 °C
86%
MsO
HO
HO
O
OH
HO
O
108
109
ingenol (
110
)
Scheme 7.23
Synthesis of ingenol (110)
O
O
O
TPAP
NMO
Me
Me
Me
DBU (
1
)
O
O
O
benzene
86-91%
86%
O
HO
O
H
O
O
O
Me
Me
Me
111
(+/-)-fraxinellone (
113
)
112
Scheme 7.24
Synthesis of (
)-fraxinellone (113)
