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Named reactions

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Search synthesis

Quinine

Chemical structure of Quinine
C20H24N2O2
Author Milan Uskokovic
Publication year 1978
Synthesis type Total synthesis
Number of steps 14 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
  1. i-Pr2NLi
  2. MeOCO2Me
THF
-78 °C to RT, 4 h, 99%
Chemical structure
H2, PtO2, HCl
70 atm
H2O
60 °C, 82%

The enantiomers were resolved with (-)-tartaric acid (29 % yield).
Chemical structure
NCS
Et2O
RT, 60 min, 92%
Chemical structure
CF3CO2H
0 °C, 50 min

See the Hofmann-Löffler-Freytag Reaction
Chemical structure
BzCl, K2CO3
PhH, H2O
RT, 2 h, 84% (2 steps)

See the Schotten-Baumann Reaction
Chemical structure
NaOH
MeOH, H2O
RT, 17 h, 99%
Chemical structure
KOt-Bu
PhH, DMSO
70 °C, 7 h, 88%
Chemical structure
CH2N2
MeOH, Et2O
RT, 90 min, 92%
Chemical structure + Chemical structure
i-Pr2NLi
THF
-78 °C to RT, 60 min, 78%
Chemical structure
H2SO4
H2O
Reflux, 24 h, 75%
Chemical structure
i-Pr2NCl, H3PO4
RT, 24 h
Chemical structure
NaBH4
THF, MeOH
RT, 20 min
Chemical structure
Ba(OH)2
MeOH, H2O
RT, 18 h, 27% (3 steps)
Chemical structure
i-Bu2AlH
PhMe
-78 °C, 33%

Quinine was selectively cristallized (as a tartrate salt) from the resulting two diastereoisomers.
Chemical structure

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