Chemistry Reference
In-Depth Information
TABLE 8C.3. Tandem Claisen - ZACA Reaction of Allyl Aryl Ethers 22
Entry
Substrate
Product
Yield (%)
% ee
1
78
78
O
OH
OH
F
F
22a
23a
2
O
OH
51
74
OH
TIPSO
TIPSO
22b
23b
3
60
73
O
OH
TIPSO
TIPSO
OH
3
3
22c
23c
4
74
76
O
OH
OH
22d
23d
5
78
75
O
OH
HO
22e
23e
6
75
80
OH
O
OH
23f
22f
HO
2
4
O
O
2
25
(dr
≥
40:1)
7 steps from allyl alcohol
18% overall yield
N
4
Ph
Me
O
O
OH
7
TBDPSO(H
2
C)
4
9
9
7
26
(dr
≥
40:1)
(-)-Spongidepsin (
24
)
7 steps from 1,5-pentanediol
20% overall yield
Scheme 8C.9.
