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Named reactions

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Search synthesis

Ingenol

Chemical structure of Ingenol
C20H28O5
Author Isao Kuwajima
Publication year 2003
Synthesis type Total synthesis
Number of steps 46 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
NaH, AllylBr
PhH
70 °C, 3.5 h

See the Williamson Ether Synthesis
Chemical structure
Cl2CHCO2H
DMF
125 °C to Reflux, 90 min, 79% (2 steps)

See the Claisen Rearrangement
Chemical structure
NBS
DMSO, H2O
10 °C, 2 h, 32%

See the Prins Reaction
Also isolated was the C2-epimer which was reverted to the starting material with zinc/ammonium chloride (52 % yield).
Chemical structure
TESCl, Imidazole
DMF
0 °C, 60 min, 99%
Chemical structure
  1. TMS2NLi
  2. ZnBr2
  3. MeCHO
THF, Et2O
-78 to 0 °C, 2 h, 71%

See the Aldol Addition
Chemical structure
(CF3CO)2O, DBU
PhH, Pyr
-23 to 0 °C, 35 min, 95%
Chemical structure
MeCO2t-Bu, i-Pr2NLi, LiBr
Et2O
-78 °C, 90 min, 91%

See the Aldol Addition
Chemical structure
  1. AlMe3
  2. i-Pr2NLi
  3. HCl, H2O
THF
-78 °C to RT, 30 h, 66%
Chemical structure
TIPSCl, DMAP
DMF
RT, 16 h, 100%
Chemical structure
LiAlH4
THF
0 to 50 °C, 4 h, 84%

The yield was 92 % brsm.
Chemical structure
Pyr.SO3, Et3N
DMSO
RT, 10 min, 97%

See the Parikh-Doering Oxidation
Chemical structure + Chemical structure
n-BuLi
THF, Et2O
-98 °C to RT, 3 h, 85%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
  1. n-BuLi
  2. (CH2O)n
THF
-78 °C to RT, 2 h, 91%

See the Fritsch-Buttenberg-Wiechell Rearrangement
Chemical structure
Ac2O, Et3N, DMAP
CH2Cl2
0 °C to RT, 30 min, 99%
Chemical structure
Co2(CO)8
CH2Cl2
RT, 60 min, 95%
Chemical structure
Reagent structure
CH2Cl2
-23 to 0 °C, 2.5 h

See the Nicholas Reaction
See the Prins Reaction
Chemical structure
Li
NH3
-78 °C, 60 min, 67% (2 steps)
Chemical structure
CHBr3, NaOH, Et3NBn+ Cl-
CH2Cl2, EtOH, H2O
0 °C, 5 h, 32%

The yield was 71% brsm.
Chemical structure
  1. MeLi, CuI
  2. MeI
Et2O
-45 °C to RT, 13 h, 95%

See the Corey-Posner, Whitesides-House Reaction
Chemical structure
t-BuOOH, Ti(Oi-Pr)4
4 Å MS
CH2Cl2
-20 to 0 °C, 60 min
Chemical structure
AlMe3
CH2Cl2
-78 °C, 60 min, 75% (2 steps)

See the Semi-Pinacol Rearrangement
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2.5 h, 93%

See the Swern Oxidation
Chemical structure + Chemical structure
DMF
100 °C

See the Mannich Reaction
Chemical structure
  1. i-Bu2AlH
  2. MeI, THF
CH2Cl2
-78 °C to RT, 30 min, 98% (2 steps)
Chemical structure
NaBH4
EtOAc
-78 to 0 °C, 30 min, 95%
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h
Chemical structure
  1. Tf2O, 2,6-Lutidine
  2. DBU
CH2Cl2
-78 °C to RT, 90 min, 83% (2 steps)
Chemical structure
n-Bu4N+ F-
THF
RT, 30 min
Chemical structure
H2Cr2O7.2Pyr
4 Å MS
CH2Cl2
RT, 2 h, 97% (2 steps)
Chemical structure
Reagent structure
DMF
120 °C, 3 h, 78%

The yield was 86% brsm.
Chemical structure
NaBH4, CeCl3
MeOH, H2O
-78 to -50 °C, 3 h

See the Luche Reduction
Chemical structure
TESCl, Imidazole
DMF
0 °C, 30 min, 99% (2 steps)
Chemical structure
OsO4
Pyr, Et2O
RT, 48 h, 59%
Chemical structure
CDI
PhH
RT, 60 min, 76%

Also isolated was the desired regioisomer (18 % yield, see next step).
Chemical structure
DMAP
PhMe
100 °C, 2 h, 27%

The yield was 99 % brsm.
Chemical structure + Chemical structure
Camphorsulfonic acid
RT, 3 h, 92%
Chemical structure
SOCl2
Pyr
RT, 30 min
Chemical structure
Ac2O
H2O
60 °C, 3 h, 96% (2 steps)
Chemical structure
Me2S, NCS, Et3N
PhMe
-23 °C to RT, 50 min, 75%

See the Corey-Kim Oxidation
Chemical structure
TESOTf, 2,6-Lutidine
CH2Cl2
0 °C, 60 min
Chemical structure
  1. i-Pr2NLi, TMSCl
  2. Et3N
THF
-78 °C, 2 h
Chemical structure
NBS
CH2Cl2
0 °C, 30 min
Chemical structure
HF
MeCN, H2O
RT, 30 min

Selectivity : 80:20
Chemical structure
+
Chemical structure
CH2I2, MeLi
THF
-78 °C, 60 min, 39% (5 steps)
Chemical structure
Zn, NH4Cl
THF, H2O
RT, 30 min, 91%
Chemical structure
KOH
MeOH
RT, 30 min, 89%
Chemical structure

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