Synthesis of Quinine
C20H24N2O2
Principal investigator | Eric N. Jacobsen |
---|---|
Publication year | 2004 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1
+
+
+
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)