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Ingenol
"This work is dedicated to the memory of Professor Josef Fried, in gratitude for his enthusiasm and encouragement during the early stages of this work."
C20H28O5
| Author | Jeffrey D. Winkler |
|---|---|
| Publication year | 2002 |
| Synthesis type | Total synthesis |
| Number of steps | 45 (linear) |
| Reference |
Browse hundreds of other total syntheses.
Part 1 of 1
+ 
TBSOTf, Et3N
CH2Cl2
RT, ON, 69 % (2 steps)
RT, ON, 69 % (2 steps)
LiAlH4
Et2O
0 °C to RT, 20 min, 100 %
0 °C to RT, 20 min, 100 %
TsCl, Et3N, DMAP
CH2Cl2
0 °C to RT, ON, 88 %
0 °C to RT, ON, 88 %
AllylMgBr, CuI
Et2O
-20 to 0 °C, 90 min, 87 %
-20 to 0 °C, 90 min, 87 %
HF
THF
RT, ON, 83 %
RT, ON, 83 %
(4-MeOPh)CH2OH
Dean-Stark
PhMe
Reflux, 11 h, 97 %
Dean-Stark
Reflux, 11 h, 97 %
(CF3CO)2O, CF3CO2H
Acetone
-78 °C to RT, ON, 93 %
-78 °C to RT, ON, 93 %
SeO2, t-BuOOH, Salicylic acid
CH2Cl2
Reflux, ON, 71 %
Reflux, ON, 71 %
+ 
+ 
LiAlH4
THF
RT, 40 min
RT, 40 min
+ 
DBU
200 °C, 24 h
TBSCl, Imidazole, DMAP
CH2Cl2
RT, 14 h, 35 % (4 steps)
Also isolated was the C6-epimer (10% yield).
RT, 14 h, 35 % (4 steps)
Also isolated was the C6-epimer (10% yield).
CHBr3, NaOH, Et3NBn+ Cl-
H2O
RT, 15 min, 100 %
RT, 15 min, 100 %
n-Bu4N+ F-
THF
RT, 3 h, 99 %
RT, 3 h, 99 %
t-BuBr
DMSO
Reflux, 10 h
Reflux, 10 h
LiCl
DMF
Reflux, 60 min, 73 % (2 steps)
Reflux, 60 min, 73 % (2 steps)
AcCl
Ac2O, Pyr
Reflux, 12 h, 80 %
Reflux, 12 h, 80 %
NBS, NaOAc, Pyr
Acetone
0 °C to RT, 12.5 h
0 °C to RT, 12.5 h
LiCl
DMF
Reflux, 60 min, 50 % (3 steps)
Reflux, 60 min, 50 % (3 steps)
i-Bu2AlH
THF
-78 °C, 30 min, 80 %
-78 °C, 30 min, 80 %
TBDPSCl, Imidazole, DMAP
CH2Cl2
RT, 12 h, 85 %
RT, 12 h, 85 %
TESOTf, 2,6-Lutidine
CH2Cl2
RT, 30 min, 83 %
RT, 30 min, 83 %
OsO4
Pyr
0 °C to RT, 12 h, 93 %
0 °C to RT, 12 h, 93 %
BzCl, Et3N, DMAP
CH2Cl2
0 °C to RT, 30 min, 82 %
0 °C to RT, 30 min, 82 %
SOCl2, Pyr
CH2Cl2
RT, 10 min
RT, 10 min
RuCl3, NaIO4
CCl4, MeCN, H2O
RT, 10 min, 79 % (2 steps)
RT, 10 min, 79 % (2 steps)
DBU
PhMe
Reflux, 12 h
Reflux, 12 h
H2SO4
THF, MeCN, H2O
RT, 60 min, 34 % (2 steps)
Also isolated was the desired TES-deprotected alcohol (40 % yield, see next step)
RT, 60 min, 34 % (2 steps)
Also isolated was the desired TES-deprotected alcohol (40 % yield, see next step)
n-Bu4N+ F-
THF
-78 °C, 4 h, 72 %
-78 °C, 4 h, 72 %
+ 
Camphorsulfonic acid
CH2Cl2
RT, 30 min, 86 %
RT, 30 min, 86 %
K2CO3
MeOH, THF
RT, 2 h, 81 %
RT, 2 h, 81 %
+ 
MeI, K2CO3
Acetone
RT, 2 h
RT, 2 h
Pd(OAc)2
MeCN
80 °C, 2 h, 20 % (3 steps)
The yield was 23 % brsm.
80 °C, 2 h, 20 % (3 steps)
The yield was 23 % brsm.
HCl
MeOH
RT, 5 h
RT, 5 h
n-Bu4N+ F-
THF
RT, 15 min, 28 % (3 steps)
RT, 15 min, 28 % (3 steps)
