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Named reactions

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Search synthesis

Quinine

Chemical structure of Quinine
C20H24N2O2
Author Robert B. Woodward
Publication year 1944
Synthesis type Formal synthesis
Number of steps 19 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
100 °C, 30 min, 94%
Chemical structure
H2SO4
H2O
0 °C to RT, 48 h, 64%

See the Pomeranz-Fritsch Isoquinoline Synthesis
Chemical structure
Piperidine, CH2O
EtOH, H2O
100 °C, 6 h, 61%

See the Betti Reaction
Chemical structure
NaOMe
MeOH
220 °C, 16 h, 65%
Chemical structure
H2, PtO2
4 atm
AcOH
RT, 18 h
Chemical structure
Ac2O
MeOH
40-50 °C, 95% (2 steps)
Chemical structure
H2, Ni (Raney)
200 atm
EtOH
150 °C, 16 h
Chemical structure
CrO3
AcOH, H2O
0 to 50 °C, ON, 30% (2 steps)

See the Jones Oxidation
Chemical structure
EtONO, NaOEt
EtOH
0 °C, 18 h, 78%
Chemical structure
H2, PtO2
3 atm
AcOH
RT, 40 h
Chemical structure
MeI, K2CO3
EtOH
Reflux, 48 h, 91% (2 steps)
Chemical structure
NaOH
H2O
180 °C, 60 min, 38%

See the Hofmann Elimination
Chemical structure
HCl
EtOH
Reflux

See the Fischer Esterification
Chemical structure
BzCl, K2CO3
CHCl3, H2O
Reflux, 2 h, 96% (2 steps)

See the Schotten-Baumann Reaction
Chemical structure + Chemical structure
NaOEt
82 °C, 14 h, 63%

See the Claisen Condensation
Chemical structure
HCl
H2O
Reflux, 4 h, 50%

The enantiomers were resolved with (+)-tartaric acid and dibenzoyl-(+)-tartaric acid (11 % yield).
Chemical structure

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Remaining...
2.4% (3 steps)

See : Chem. Ber. 1918, 51, 466; Angew. Chem. Int. Ed. 2008, 47, 1736.
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