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Named reactions

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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."

Chemical structure of Ingenol
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
Chemical structure
+
Chemical structure
Li, NH3
THF, t-BuOH
-78 to -5 °C, 75 min

See the Michael Addition
Chemical structure
TBSOTf, Et3N
CH2Cl2
RT, ON, 69% (2 steps)
Chemical structure
LiAlH4
Et2O
0 °C to RT, 20 min, 100%
Chemical structure
TsCl, Et3N, DMAP
CH2Cl2
0 °C to RT, ON, 88%
Chemical structure
AllylMgBr, CuI
Et2O
-20 to 0 °C, 90 min, 87%
Chemical structure
HF
THF
RT, ON, 83%
Chemical structure
  1. i-Pr2NLi
  2. MeO2CCN
THF, HMPA
-78 °C, 90 min, 89%

See the Claisen Condensation
Chemical structure
(4-MeOPh)CH2OH
Dean-Stark
PhMe
Reflux, 11 h, 97%
Chemical structure
(CF3CO)2O, CF3CO2H
Acetone
-78 °C to RT, ON, 93%
Chemical structure
SeO2, t-BuOOH, Salicylic acid
CH2Cl2
Reflux, ON, 71%
Chemical structure
Ph3P, C2Cl6
CH2Cl2, Et2O
0 °C, 60 min, 93%

See the Appel Reaction
Chemical structure
MeCN, Acetone
0 °C, 16 h, 60%

Selectivity : 83:17
See the De Mayo Reaction
Chemical structure
+
Chemical structure
K2CO3
MeOH
RT, 36 h

See the De Mayo Reaction
Chemical structure
+
Chemical structure
LiAlH4
THF
RT, 40 min
Chemical structure
+
Chemical structure
DBU
200 °C, 24 h
Chemical structure
TBSCl, Imidazole, DMAP
CH2Cl2
RT, 14 h, 35% (4 steps)

Also isolated was the C6-epimer (10% yield).
Chemical structure
CHBr3, NaOH, Et3NBn+ Cl-
H2O
RT, 15 min, 100%
Chemical structure
  1. MeLi, CuSCN
  2. MeI
Et2O
-78 to -15 °C, 3.5 h, 72%

See the Corey-Posner, Whitesides-House Reaction
Chemical structure
n-Bu4N+ F-
THF
RT, 3 h, 99%
Chemical structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
0 °C to RT, 6 h, 89%

See the Dess-Martin Oxidation
Chemical structure
t-BuBr
DMSO
Reflux, 10 h
Chemical structure
LiCl
DMF
Reflux, 60 min, 73% (2 steps)
Chemical structure
AcCl
Ac2O, Pyr
Reflux, 12 h, 80%
Chemical structure
NBS, NaOAc, Pyr
Acetone
0 °C to RT, 12.5 h
Chemical structure
LiCl
DMF
Reflux, 60 min, 50% (3 steps)
Chemical structure
i-Bu2AlH
THF
-78 °C, 30 min, 80%
Chemical structure
OsO4, NMO
THF, t-BuOH, H2O
RT, 2 h, 69%

See the Upjohn Dihydroxylation
Chemical structure
TBDPSCl, Imidazole, DMAP
CH2Cl2
RT, 12 h, 85%
Chemical structure
TESOTf, 2,6-Lutidine
CH2Cl2
RT, 30 min, 83%
Chemical structure
OsO4
Pyr
0 °C to RT, 12 h, 93%
Chemical structure
BzCl, Et3N, DMAP
CH2Cl2
0 °C to RT, 30 min, 82%
Chemical structure
SOCl2, Pyr
CH2Cl2
RT, 10 min
Chemical structure
RuCl3, NaIO4
CCl4, MeCN, H2O
RT, 10 min, 79% (2 steps)
Chemical structure
DBU
PhMe
Reflux, 12 h
Chemical structure
H2SO4
THF, MeCN, H2O
RT, 60 min, 34% (2 steps)

Also isolated was the desired TES-deprotected alcohol (40 % yield, see next step)
Chemical structure
n-Bu4N+ F-
THF
-78 °C, 4 h, 72%
Chemical structure + Chemical structure
Camphorsulfonic acid
CH2Cl2
RT, 30 min, 86%
Chemical structure
K2CO3
MeOH, THF
RT, 2 h, 81%
Chemical structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
0 to 25 °C, 4 h, 96%

See the Dess-Martin Oxidation
Chemical structure + Chemical structure
i-Pr2NLi
Et2O
-78 °C, 2 h

See the Claisen Condensation
Chemical structure
MeI, K2CO3
Acetone
RT, 2 h
Chemical structure
Pd(OAc)2
MeCN
80 °C, 2 h, 20% (3 steps)

The yield was 23 % brsm.
Chemical structure
NaBH4, CeCl3
MeOH
0 °C, 60 min

See the Luche Reduction
Chemical structure
HCl
MeOH
RT, 5 h
Chemical structure
n-Bu4N+ F-
THF
RT, 15 min, 28% (3 steps)
Chemical structure

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