Chemistry Reference
In-Depth Information
OH
OAc
Pd
2
(dba)
3
, THF
97%
O
O
OAc
OH
144
142
Ph
2
P
NH HN
PPh
2
O
O
K
2
Os(OH)
4
(
R
,
R
)-DPPBA
143
70% after
one recycle
(DHQD)
2
AQN
K
3
[Fe(CN)
6
]
K
2
Os(OH)
4
(DHQ)
2
AQN
C
10
H
21
HO
O
O
O
O
K
3
[Fe(CN)
6
]
86%
HO
HO
145
146
O
C
10
H
21
C
10
H
21
24
15
OH
( )
9
O
O
O
O
1
HO
OH
OH
O
AcO
Keinan's
procedure
147
uvaricin
Scheme 10-26. Formal total synthesis of uvaricin by Burke and Jiang.
O
149
O
C
12
H
25
C
12
H
25
I
O
O
O
MOMO
MOMO
MOMO
MOMO
O
150
148
OTs
O
C
12
H
25
C
12
H
25
O
O
MOMO
MOMO
MOMO
MOMO
151
152
1. AD-mix-α
2. Triton B
O
I
OH
1. H
2
, Rh(PPh
3
)
3
Cl
154
O
C
12
H
25
O
O
Pd(0)
2. BF
3
⋅OEt
2
, Me
2
S
MOMO
MOMO
153
OH
O
22
18
10
C
12
H
25
O
O
O
14
HO
HO
4-deoxygigantecin
Scheme 10-27. Total synthesis of 4-deoxygigantecin by Makabe et al.
Search WWH ::
Custom Search