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Named reactions

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Search synthesis

Quinine

"This paper is dedicated to the memory and legacy of Prof. Satoru Masamune."

Chemical structure of Quinine
C20H24N2O2
Author Eric N. Jacobsen
Publication year 2004
Synthesis type Total synthesis
Number of steps 18 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
n-BuLi
THF
-78 to 0 °C, 2 h, 84%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
Reagent structure
Methyl Cyanoacetate
Cyclohexane, t-BuOH
RT, 48 h, 91%

Selectivity : 96:04 er
See the Michael Addition
Chemical structure
H2, Ni (Raney)
43 atm
MeOH
80 °C, 14 h, 89%

Selectivity : 47:63 R/S
Chemical structure
i-Pr2NLi, H2O
THF
-78 °C to RT, 50 min

Selectivity : 75:25 R/S
Chemical structure
LiAlH4
THF
0 to 35 °C, 11 h
Chemical structure
(BnOCO)2O, Et3N
CH2Cl2
0 °C to RT, 4 h, 51% (3 steps)

Also isolated was the C3-epimer (19 % yield).
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
RT, 60 min

See the Ley-Griffith Oxidation
Chemical structure
Ph3P+CH3 Br-, KOt-Bu
THF
0 °C to RT, 13 h, 73% (2 steps)

See the Wittig Reaction
Chemical structure
n-Bu4N+ F-
THF
0 °C, 4 h
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
RT, 60 min, 86% 2 steps)

See the Ley-Griffith Oxidation
Chemical structure + Chemical structure
CrCl2
THF
RT, 12 h, 79%

See the Takai Reaction
Chemical structure + Chemical structure
Reagent structure
Pd(OAc)2, K3PO4
THF
RT, 16 h, 89%

See the Suzuki Coupling
Chemical structure
AD-mix β, MsNH2
t-BuOH
0 °C, 12 h, 88%

See the Sharpless Asymmetric Dihydroxylation
Chemical structure
MeC(OMe)3, Pyr.TsOH
CH2Cl2
RT, 12 h
Chemical structure
AcBr
CH2Cl2
0 °C to RT, 6 h
Chemical structure
+
Chemical structure
K2CO3
MeOH
RT, 2 h, 81% (3 steps)
Chemical structure
Et2AlCl, PhSMe
CH2Cl2
0 °C to RT, 8 h
Chemical structure
µW
MeCN
185 °C, 20 min, 68% (2 steps)
Chemical structure

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