Synthesis of Quinine
C20H24N2O2
Principal investigator | Yuichi Kobayashi |
---|---|
Publication year | 2004 |
Synthesis type | Total |
Number of steps | 24 (linear) |
References |
Part 1 of 1
+
LiAlH4
Imidazole,
TBDPSCl
63% (2 steps)
NaBH4
Et3N,
t-BuCOCl
CH2Cl2
66% (3 steps)
NaBH4,
O3
n-PrOH
-78 °C, 81%
BnNH2
Dioxane
100 °C, 98%
ClCO2Et
PhMe
99%
NaOEt
EtOH
Reflux
MeLi
0 °C
BzCl
61% (2 steps)
n-Bu4N+ F-
THF
HCrO3Cl.Pyr
CH2Cl2
80% (2 steps)
MeC(OMe)3,
Pyr.TsOH
CH2Cl2
TMSCl
K2CO3
MeOH
96% (3 steps)
i-Bu2AlH
PhMe
DMF
160 °C, 66% (2 steps)