Synthesis of Doliculide

C27H41IN2O6
Principal investigator | Arun K. Ghosh |
---|---|
Publication year | 2001 |
Synthesis type | Total |
Number of steps | 40 (3 parts) |
References |
Part 1 of 3
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i-Bu2AlH
CH2Cl2
0 °C, 30 min, 85%


i-Bu2AlH
CH2Cl2
-40 °C, 30 min, 93%



(CH2NMe2)2,
n-BuLi
4 Å MS
Et2O
-78 °C to RT, 30 min, 90%

- 9-BBN
- NaOH , H2O2 , H2O
THF
0 °C to RT, 4 h, 80%



i-Bu2AlH
CH2Cl2
-40 °C, 30 min, 90%



(CH2NMe2)2,
n-BuLi
4 Å MS
Et2O
-78 °C to RT, 30 min, 74% (2 steps)

- O3
- Ph3P
CH2Cl2
-78 °C to RT, 4 h


i-Bu2AlH
CH2Cl2
-40 °C, 30 min, 90%





Pd2(dba)3.CHCl3,
HCO2H,
Et3N,
n-Bu3P
Dioxane
RT, 10 h, 90%

TBSOTf,
Et3N
CH2Cl2
0 °C, 15 min

i-Bu2AlH
CH2Cl2
-40 °C, 30 min, 80% (2 steps)

t-BuOOH,
Ti(Oi-Pr)4,
(+)-DET
4 Å MS
CH2Cl2
-23 °C, 20.5 h, 91%

MsCl,
Et3N,
DMAP
CH2Cl2
-78 to 0 °C, 2 h


(CH2NMe2)2,
n-BuLi
4 Å MS
Et2O
-78 °C to RT, 30 min, 84% (3 steps)

Pd/C,
H2
1 atm
THF
RT, 6 h, 84%



Boc2O,
DMAP
t-BuOH
30 °C, 15 h, 57% (3 steps)

Part 2 of 3
+

Imidazole,
TIPSCl
DMF
0 °C to RT, 2 h, 98%

MeI,
NaH
DMF, THF
60 °C, 20 h

CF3CO2H
CH2Cl2
0 °C to RT, 3 h, 50% (2 steps)


HOBt,
EDC
DMF
0 °C to RT, 20 h, 90%

LiOH
H2O, THF
0 °C, 60 min, 100%

Part 3 of 3
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CF3CO2H
CH2Cl2
0 °C to RT, 3 h

DMAP,
BOP reagent
CH2Cl2
0 °C to RT, 24 h, 82% (2 steps)

NH3
H2O, MeOH
RT, 60 min, 88%

n-Bu4N+ F-
THF
0 °C, 15 min, 98%
