Synthesis of Quinine

C20H24N2O2
Principal investigator | Yuichi Kobayashi |
---|---|
Publication year | 2004 |
Synthesis type | Total |
Number of steps | 24 (linear) |
References |
Part 1 of 1
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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)
