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Ingenol
"This report is dedicated to Prof. Amos B. Smith, III on the occasion of his 60th birthday."
C20H28O5
| Author | John L. Wood |
|---|---|
| Publication year | 2004 |
| Synthesis type | Total synthesis |
| Number of steps | 33 (linear) |
| References |
Browse hundreds of other total syntheses.
Part 1 of 1
(CH2OH)2, TsOH
Dean-Stark
PhH
Reflux, 12 h, 35 % (2 steps)
The product was separated from the resulting four diastereoisomers.
Dean-Stark
Reflux, 12 h, 35 % (2 steps)
The product was separated from the resulting four diastereoisomers.
LiAlH4
Et2O
RT, 2 h
RT, 2 h
HCl
Acetone
RT, 30 min, 95 % (2 steps)
RT, 30 min, 95 % (2 steps)
Ac2O, DMAP
Pyr
RT, 30 min, 96 %
RT, 30 min, 96 %
DBU
PhH
Reflux, 10 h, 88 %
Reflux, 10 h, 88 %
+ 
BF3.OEt2
PhMe
-78 °C, 85 min, 59 %
See the Diels-Alder Reaction
The product was separated from the resulting three diastereoisomers.
-78 °C, 85 min, 59 %
See the Diels-Alder Reaction
The product was separated from the resulting three diastereoisomers.
NaIO4
MeOH, THF, H2O
RT, 60 min
RT, 60 min
(CH2OH)2, Pyr.TsOH
Dean-Stark
PhH
Reflux, 4 h, 73 % (3 steps)
Dean-Stark
Reflux, 4 h, 73 % (3 steps)
+ 
KH
THF
Reflux, ON, 98 %
Reflux, ON, 98 %
HCl
THF, H2O
Reflux, 3 h
Reflux, 3 h
NaBH4
EtOH, THF
0 °C, 15 min, 77 % (2 steps)
0 °C, 15 min, 77 % (2 steps)
KOt-Bu
DMSO
RT, ON, 94 % (2 steps)
RT, ON, 94 % (2 steps)
SeO2, t-BuOOH
CH2Cl2, AcOH
0 °C to RT, 2 h, 49 %
The yield was 70 % brsm.
0 °C to RT, 2 h, 49 %
The yield was 70 % brsm.
RhCl3
Sealed tube
EtOH, H2O
115 °C, 35 min, 74 %
Sealed tube
115 °C, 35 min, 74 %
KOt-Bu, O2, P(OMe)3
THF, t-BuOH
-40 °C, 45 min, 94 %
-40 °C, 45 min, 94 %
VO(acac)2, t-BuOOH
PhH
10 °C to RT, 10 h, 73 %
10 °C to RT, 10 h, 73 %
TMSOTf, Et3N
CH2Cl2
-10 to -5 °C, 60 min, 72 %
-10 to -5 °C, 60 min, 72 %
NaBH4
MeOH
RT, 5 h
RT, 5 h
2,2-Dimethoxypropane, Pyr.TsOH
CH2Cl2
Reflux, 30 min, 86 % (2 steps)
Reflux, 30 min, 86 % (2 steps)
DDQ
CH2Cl2
RT, 18 h, 90 %
RT, 18 h, 90 %
MsCl, Et3N
CH2Cl2
-78 °C, 45 min, 96 %
-78 °C, 45 min, 96 %
PhSH, Li2CO3
DMF
55 °C, 5 h, 76 %
55 °C, 5 h, 76 %
(NH4)6Mo7O24.4H2O, H2O2
EtOH, H2O
RT, 6 h, 97 %
RT, 6 h, 97 %
DBU
PhH
Reflux, 5 h, 47 %
Also isolated was a mixture of E/Z exocyclic sulfones (47 % yield) which could be equilibrated to afford the desired allylic sulfone.
Reflux, 5 h, 47 %
Also isolated was a mixture of E/Z exocyclic sulfones (47 % yield) which could be equilibrated to afford the desired allylic sulfone.
Na(Hg), Na2HPO4
MeOH
-20 to -10 °C, 25 min, 76 %
-20 to -10 °C, 25 min, 76 %
HCl
THF, H2O
RT, 5 h, 92 %
RT, 5 h, 92 %
SeO2, SiO2
THF
80 °C, 2 h, 40 %
The yield was 89 % brsm.
80 °C, 2 h, 40 %
The yield was 89 % brsm.
