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C
8
H
17
SnBu
3
C
8
H
17
OHC
92
OMOM
OBn
OBn
O
OTBS
OH
OTBS
TBS
TBSO
InBr
3
MOMO
91
93
Bu
3
Sn
( )
3
C
10
H
21
C
10
H
21
O
95
OMOM
O
O
OH
O
OMOM
O
OTBS
TBS
MOMO
O
MOMO
Ts
TBS
TBS
InBr
3
Ts
94
96
OH
O
I
1.
2. TsNHNH
2
, NaOAc
C
10
H
21
9
8
1. TsCl
O
O
O
2. TBAF
MOMO
OMOM
3. HCl, THF, MeOH
97
OH
O
Bu
24
15
O
O
1
HO
OH
O
asimicin
threo-trans-threo-trans-threo
Scheme 10-19. Total synthesis of asimicin by Marshall et al.
OHC
OBn
TBSO
OTBS
BF
3
.OEt
2
( )
3
Bu
91
( )
3
SnBu
3
Bu
TBS
OMOM
BF
3
⋅OEt
2
O
Sn
OMOM
OTBS
Bu
3
99
100
( )
3
Bu
Bu
( )
( )
5
OBn
3
O
O
O OTBS
TBS
OH
OMOM
TBS
O
O
TBS
O
MOMO
MOM
102
101
2. TsNHNH
2
, NaOAc
3. HCl, THF, MeOH
O
I
1.
O
103
O
30
Bu
24
15
O
O
1
O
OH
HO
OH
bullanin
erythro-trans-threo-trans-threo
Scheme 10-20. Total synthesis of bullalin by Marshall et al.
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