Chemistry Reference
In-Depth Information
Me
Me
Me
Me
Me
H
O
H
H
Br
Me
O
O
Me
4
Me
Me
+
O
O
O
LDA
THF-DMPU
-78 to -69 °C
H
H
H
H
2
C
H
2
C
H
2
C
206
207
(+)-coraxeniolide A (
208
)
50%
207
:
208
= 5.7 : 1
207
:
208
= 1 : 3
TBD (
7
), toluene, 80%
Scheme 7.48
Synthesis of (
þ
)-coraxeniolide A (208)
TBSO
TBSO
Me
Me
Me
Me
Ph
O
1. LDA
MoOPH, 80%
Ph
O
Me
Me
OAc
O
O
10
10
H
H
2. Ac
2
O, Py, 92%
O
O
H
2
C
H
2
C
Me
O
Me
O
OMe
OMe
Cl
Cl
Me
Me
Me
Me
209
210
DBN (
2
)
toluene, reflux
68%
(92% conversion)
TBSO
Me
Me
Ph
O
Me
OAc
O
10
taxol (
157
)
H
O
H
2
C
Me
O
OMe
Cl
Me
Me
211
Scheme 7.49
Synthesis of taxol (157)
