Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigatorYuichi Kobayashi
Publication year2004
Synthesis typeTotal
Number of steps 24 (linear)
References
Part 1 of 1
intermediate structure
Dimethyl malonate, KOt-Bu, Pd(PPh3)4
THF
50 °C, 3 h
intermediate structure
KI
DMF
125 °C, , 70% (2 steps)
intermediate structure
LiAlH4
intermediate structure
Imidazole, TBDPSCl
63% (2 steps)
intermediate structure
VinylOEt, Hg(OAc)2
190 °C
intermediate structure
NaBH4
intermediate structure
Et3N, t-BuCOCl
CH2Cl2
66% (3 steps)
intermediate structure
NaBH4, O3
n-PrOH
-78 °C, , 81%
intermediate structure
I2, Imidazole, Ph3P
88%
See the Appel Reaction
intermediate structure
BnNH2
Dioxane
100 °C, , 98%
intermediate structure
ClCO2Et
PhMe
99%
intermediate structure
NaOEt
EtOH
Reflux
intermediate structure
  1. n-Bu3P
  2. H2O
  3. H2O2
  4. o-NO2PhSeCN
THF
77% (2 steps)
intermediate structure
MeLi
0 °C
intermediate structure
BzCl
61% (2 steps)
intermediate structure
n-Bu4N+ F-
THF
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
80% (2 steps)
intermediate structure + intermediate structure
NaH
THF
RT, , 82%
intermediate structure
AD-mix B
0 °C to RT, , 89%
intermediate structure
MeC(OMe)3, Pyr.TsOH
CH2Cl2
intermediate structure
TMSCl
intermediate structure intermediate structure
K2CO3
MeOH
96% (3 steps)
intermediate structure
i-Bu2AlH
PhMe
intermediate structure
DMF
160 °C, , 66% (2 steps)
intermediate structure