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 225 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

Quinine

Chemical structure of Quinine
C20H24N2O2
Author Milan Uskokovic
Publication year 1970
Synthesis type Total synthesis
Number of steps 10 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
NaN3
PPA
120 °C, 30 min, 63 %

See the Schmidt Reaction
Also isolated was 13 % of the enamine regioisomer.
Chemical structure
H2, Rh/Al2O3, HCl
EtOH, H2O
RT, 75 min, 100 %
Chemical structure
N2O4, NaOAc
CCl4
-70 to 0 °C, 30 min, 100 %
Chemical structure
125 °C, 60 min, 49 %
Chemical structure
CH2N2
Et2O
RT, 15 min, 100 %
Chemical structure
+
Chemical structure
i-Pr2NLi
THF
-78 °C to RT, 60 min, 78 %
Chemical structure
i-Bu2AlH
PhMe
-78 °C, 80 min, 85 %

Selectivity : 66:33 S/R
The enantiomers were resolved with dibenzoyl-(+)-tartaric acid.
Chemical structure
BF3.OEt2
AcOH
50 °C, 18 h, 96 %

See the Fischer Esterification
Chemical structure
NaOAc
AcOH, PhH
Reflux, 14 h, 80 %

Selectivity : 43:57 S/R
Chemical structure
O2, KOt-Bu
DMSO, t-BuOH
RT, 20 min, 32 %

Quinine was selectively cristallized (as a tartrate salt) from the resulting four diastereoisomers.
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