Synthesis of Quinine

C20H24N2O2
Principal investigator | Eric N. Jacobsen |
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Publication year | 2004 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1
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H2,
Ni (Raney)
43 atm
MeOH
80 °C, 14 h, 89%

H2O,
i-Pr2NLi
THF
-78 °C to RT, 50 min

LiAlH4
THF
0 to 35 °C, 11 h

(BnOCO)2O,
Et3N
CH2Cl2
0 °C to RT, 4 h, 51% (3 steps)
"Also isolated was the C3-epimer (19 % yield)."



n-Bu4N+ F-
THF
0 °C, 4 h







MeC(OMe)3,
Pyr.TsOH
CH2Cl2
RT, 12 h

AcBr
CH2Cl2
0 °C to RT, 6 h


K2CO3
MeOH
RT, 2 h, 81% (3 steps)

Et2AlCl,
PhSMe
CH2Cl2
0 °C to RT, 8 h

µW
MeCN
185 °C, 20 min, 68% (2 steps)
