Ретросинтез Wickerol A
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Категория: ХимияХимия

Ретросинтез Wickerol A

1. Ретросинтез Wickerol A

2.

OTBS
AlBr3 /AlMe 3
+
p-TSA
(86%)
(66%)
O
O
4
6
8
OTBS
Me
1) LAH (58%)
2) Burgess rgt. (91%)
3) OsO 4 , NMO (81%)
PPh 3 , C 2 Cl6
then NaBH 4
O
H
OH
(49%)
O
H
OH
9
O
O
O
S
O
N
N
+
B u rg e s s rg t.
s in - e lim in a t io n
H
OTBS
OTBS
Me
8
H
O
H
O
OTBS
5
OTBS
Me
OTBS
Me
Me
H
OH
10

3.

OTBS
Me
Martin's
sulfurane
1) MOMCl (81%)
2) DIBAL-H (97%)
10
H
HO
H
+
(99%,
12:13=2:1)
H
OMOM
OTBS
Me
Mn(OAc)3,
t-BuOOH
12
O
1) TBAF (76%)
2) MsCl (89%)
OMS
Me
H
H
14
CF 3
O
CF 3
S
15
M artin's
sulfurane
elim ination of hydroxy group
O
CF 3
H
H
OMOM
13
O
KHMDS
H
Me
(71%)
H
OMOM
OMOM
CF 3
H
12
(62%)
H
H
H
OMOM
11
O
OTBS
Me
OTBS
Me
H
OMOM
16

4.

O
1) LAH (95%)
2) KHMDS, CS 2, MeI (95%)
3) AlBN, Bu 3SnH (79%)
Me
CuCN, MeLi, BF 3*Et2O
16
(65%)
H
H
Me
4) HCl (94%)
5) DMP (95%)
H
O
OMOM
17
18
Me
Me
Me
Ph3P=CH 2
Co(acac)2, PhSiH 3, O 2
+
18
(65%)
H
H
H
H
OH
19
H
wickerol A (1)
(31%)
H
H
OH
3-epi-wickerol A (20)
(28%)
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