Synthesis of Quinine

Structure of Quinine

C20H24N2O2

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