Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigatorMilan Uskokovic
Publication year1970
Synthesis typeTotal
Number of steps 10 (linear)
References
J. Am. Chem. Soc. 1970, 92, 203. J. Am. Chem. Soc. 1970, 92, 204. J. Am. Chem. Soc. 1978, 100, 571.
Part 1 of 1
intermediate structure
NaN3
PPA
120 °C, 30 min, 63%
See the Schmidt Reaction
"Also isolated was 13 % of the enamine regioisomer."
intermediate structure
Rh/Al2O3, HCl, H2
EtOH, H2O
RT, 75 min, 100%
intermediate structure
NaOAc, N2O4
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%
See the Fischer-Speier Esterification
intermediate structure
NaOAc
AcOH, PhH
Reflux, 14 h, 80%
intermediate structure
KOt-Bu, O2
DMSO, t-BuOH
RT, 20 min, 32%
"Quinine was selectively cristallized (as a tartrate salt) from the resulting four diastereoisomers."
intermediate structure
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