Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigatorMilan Uskokovic
Publication year1970
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure
NaN3
PPA
120 °C, 30 min, 63%
"Also isolated was 13 % of the enamine regioisomer."
intermediate structure
H2, Rh/Al2O3, HCl
EtOH, H2O
RT, 75 min, 100%
intermediate structure
N2O4, NaOAc
CCl4
-70 to 0 °C, 30 min, 100%
intermediate structure
125 °C, 60 min, 49%
intermediate structure
CH2N2
Et2O
RT, 15 min, 100%
intermediate structure + intermediate structure
i-Pr2NLi
THF
-78 °C to RT, 60 min, 78%
intermediate structure
i-Bu2AlH
PhMe
-78 °C, 80 min, 85%
"The enantiomers were resolved with dibenzoyl-(+)-tartaric acid."
intermediate structure
BF3.OEt2
AcOH
50 °C, 18 h, 96%
intermediate structure
NaOAc
AcOH, PhH
Reflux, 14 h, 80%
intermediate structure
O2, KOt-Bu
DMSO, t-BuOH
RT, 20 min, 32%
"Quinine was selectively cristallized (as a tartrate salt) from the resulting four diastereoisomers."
intermediate structure