Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigatorGilbert Stork
Publication year2001
Synthesis typeTotal
Number of steps 17 (linear)
References
Part 1 of 1
intermediate structure
AlMe3, Et2NH
CH2Cl2
0 °C to RT, ON, 82%
intermediate structure
Imidazole, TBSCl
CH2Cl2
RT, 18 h, 97%
intermediate structure + intermediate structure
i-Pr2NLi
THF
-78 °C to RT, 5 h, 79%
intermediate structure
Pyr.TsOH
EtOH
RT, ON, 93%
intermediate structure
Xylene(s)
Reflux, 12 h, 97%
intermediate structure
i-Bu2AlH
THF
-78 °C, 5 h
intermediate structure
TMS2NK, Ph3P+CH2OMe Cl-
THF
-78 °C to RT, ON, 75% (2 steps)
See the Wittig Reaction
intermediate structure
(PhO)2P(O)N3, DEAD, Ph3P
THF
0 °C, 24 h, 95%
intermediate structure
HCl
CH2Cl2, H2O, THF
RT, 8 h, 78%
intermediate structure + intermediate structure
i-Pr2NLi
THF
-78 to 0 °C, 65 min, 72%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 90 min, 85%
See the Swern Oxidation
intermediate structure
Ph3P
THF
Reflux, 3 h, 81%
See the Wittig Reaction
intermediate structure
NaBH4
MeOH, THF
RT, 3 h, 91%
intermediate structure
HF
H2O, MeCN
RT, 60 min, 95%
intermediate structure
MsCl, Pyr
CH2Cl2
RT, ON
intermediate structure
MeCN
Reflux, 3 h, 68% (2 steps)
intermediate structure
NaH, O2
DMSO
70 °C, 45 min, 78%
intermediate structure