Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigatorRobert B. Woodward
Publication year1944
Synthesis typeFormal
Number of steps 17 (linear)
References
J. Am. Chem. Soc. 1944, 66, 849. J. Am. Chem. Soc. 1945, 67, 860.
Part 1 of 1
intermediate structure + intermediate structure
100 °C, 30 min, 94%
intermediate structure
H2SO4
H2O
0 °C to RT, 48 h, 64%
See the Pomeranz-Fritsch Isoquinoline Synthesis
intermediate structure
CH2O, Piperidine
EtOH, H2O
100 °C, 6 h, 61%
See the Betti Reaction
intermediate structure
NaOMe
MeOH
220 °C, 16 h, 65%
intermediate structure
H2, PtO2
4 atm
AcOH
RT, 18 h
intermediate structure
Ac2O
MeOH
40-50 °C, 95% (2 steps)
intermediate structure
H2, Ni (Raney)
200 atm
EtOH
150 °C, 16 h
intermediate structure
CrO3
AcOH, H2O
0 to 50 °C, ON, 30% (2 steps)
See the Jones Oxidation
intermediate structure
NaOEt, EtONO
EtOH
0 °C, 18 h, 78%
intermediate structure
H2, PtO2
3 atm
AcOH
RT, 40 h
intermediate structure
K2CO3, MeI
EtOH
Reflux, 48 h, 91% (2 steps)
intermediate structure
NaOH
H2O
180 °C, 60 min, 38%
See the Hofmann Elimination
intermediate structure
HCl
EtOH
Reflux
See the Fischer-Speier Esterification
intermediate structure
BzCl, K2CO3
CHCl3, H2O
Reflux, 2 h, 96% (2 steps)
See the Schotten-Baumann Reaction
intermediate structure + intermediate structure
NaOEt
82 °C, 14 h, 63%
See the Claisen Condensation
intermediate structure
HCl
H2O
Reflux, 4 h, 50%
"The enantiomers were resolved with (+)-tartaric acid and dibenzoyl-(+)-tartaric acid (11% yield)"
intermediate structure
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Remaining...
2.4% (3 steps)
"See : Chem. Ber. 1918, 51, 466; Angew. Chem. Int. Ed. 2008, 47, 1736."
intermediate structure