Synarchive logo
Google+ Facebook Twitter RSS Feed
Support this website
Synarchive is free but requires a lot of work. If you enjoy and find it useful, please support us by making a donation.
Named reactions

Get references and more from over 229 named organic chemical reaction

Go to the named reaction index

Protecting Groups

Get the conditions needed to install/remove a wide range of protecting groups.

Go to the protecting groups index

Search synthesis

Ingenol

"This report is dedicated to Prof. Amos B. Smith, III on the occasion of his 60th birthday."

Chemical structure of Ingenol
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
Chemical structure
MeLi, CuCN
Et2O
-78 °C, 2 h

See the Michael Addition
Chemical structure
(CH2OH)2, TsOH
Dean-Stark
PhH
Reflux, 12 h, 35% (2 steps)

The product was separated from the resulting four diastereoisomers.
Chemical structure
LiAlH4
Et2O
RT, 2 h
Chemical structure
HCl
Acetone
RT, 30 min, 95% (2 steps)
Chemical structure
Ac2O, DMAP
Pyr
RT, 30 min, 96%
Chemical structure
DBU
PhH
Reflux, 10 h, 88%
Chemical structure + Chemical structure
BF3.OEt2
PhMe
-78 °C, 85 min, 59%

See the Diels-Alder Reaction
The product was separated from the resulting three diastereoisomers.
Chemical structure
Grubbs catalyst (2nd gen.), C2H4
CH2Cl2
RT, 12 h, 98%

See the Olefin Metathesis
Chemical structure
OsO4, NMO
THF, H2O
RT, 8 h

See the Upjohn Dihydroxylation
Chemical structure
NaIO4
MeOH, THF, H2O
RT, 60 min
Chemical structure
(CH2OH)2, Pyr.TsOH
Dean-Stark
PhH
Reflux, 4 h, 73% (3 steps)
Chemical structure + Chemical structure
KH
THF
Reflux, ON, 98%
Chemical structure
Grubbs-Hoveyda catalyst (2nd gen.)
PhMe
RT, 30 h, 76%

See the Olefin Metathesis
Chemical structure
HCl
THF, H2O
Reflux, 3 h
Chemical structure
NaBH4
EtOH, THF
0 °C, 15 min, 77% (2 steps)
Chemical structure
I2, Ph3P, Imidazole
THF
0 °C, 3 h

See the Appel Reaction
Chemical structure
KOt-Bu
DMSO
RT, ON, 94% (2 steps)
Chemical structure
SeO2, t-BuOOH
CH2Cl2, AcOH
0 °C to RT, 2 h, 49%

The yield was 70 % brsm.
Chemical structure
Dess-Martin Periodinane
CH2Cl2
-40 to 10 °C, 90 min, 74%

See the Dess-Martin Oxidation
Chemical structure
RhCl3
Sealed tube
EtOH, H2O
115 °C, 35 min, 74%
Chemical structure
KOt-Bu, O2, P(OMe)3
THF, t-BuOH
-40 °C, 45 min, 94%
Chemical structure
VO(acac)2, t-BuOOH
PhH
10 °C to RT, 10 h, 73%
Chemical structure
TMSOTf, Et3N
CH2Cl2
-10 to -5 °C, 60 min, 72%
Chemical structure
NaBH4
MeOH
RT, 5 h
Chemical structure
2,2-Dimethoxypropane, Pyr.TsOH
CH2Cl2
Reflux, 30 min, 86% (2 steps)
Chemical structure
DDQ
CH2Cl2
RT, 18 h, 90%
Chemical structure
MsCl, Et3N
CH2Cl2
-78 °C, 45 min, 96%
Chemical structure
PhSH, Li2CO3
DMF
55 °C, 5 h, 76%
Chemical structure
(NH4)6Mo7O24.4H2O, H2O2
EtOH, H2O
RT, 6 h, 97%
Chemical structure
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.
Chemical structure
Na(Hg), Na2HPO4
MeOH
-20 to -10 °C, 25 min, 76%
Chemical structure
HCl
THF, H2O
RT, 5 h, 92%
Chemical structure
SeO2, SiO2
THF
80 °C, 2 h, 40%

The yield was 89 % brsm.
Chemical structure

Report an error in this part

comments powered by Disqus
homepage - authors - molecules - named reactions - protecting groups - advanced search - contact
© 2011-2017 SynArchive