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Named reactions

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Search synthesis

Quinine

Chemical structure of Quinine
C20H24N2O2
Author Yuichi Kobayashi
Publication year 2004
Synthesis type Total synthesis
Number of steps 24 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Dimethyl malonate, Pd(PPh3)4, KOt-Bu
THF
50 °C, 3 h

See the Tsuji-Trost Reaction
Chemical structure
KI
DMF
125 °C, 70% (2 steps)

See the Krapcho Decarboxylation
Chemical structure
LiAlH4
Chemical structure
TBDPSCl, Imidazole
63% (2 steps)
Chemical structure
VinylOEt, Hg(OAc)2
190 °C

See the Claisen Rearrangement
Chemical structure
NaBH4
Chemical structure
t-BuCOCl, Et3N
CH2Cl2
66% (3 steps)
Chemical structure
O3, NaBH4
n-PrOH
-78 °C, 81%
Chemical structure
I2, Ph3P, Imidazole
88%

See the Appel Reaction
Chemical structure
BnNH2
Dioxane
100 °C, 98%
Chemical structure
ClCO2Et
PhMe
99%
Chemical structure
NaOEt
EtOH
Reflux
Chemical structure
  1. o-NO2PhSeCN, n-Bu3P
  2. H2O2, H2O
THF
77% (2 steps)

See the Grieco Dehydration
Chemical structure
MeLi
0 °C
Chemical structure
BzCl
61% (2 steps)
Chemical structure
n-Bu4N+ F-
THF
Chemical structure
HCrO3Cl.Pyr
CH2Cl2
80% (2 steps)
Chemical structure + Chemical structure
NaH
THF
RT, 82%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
AD-mix β
0 °C to RT, 89%

See the Sharpless Asymmetric Dihydroxylation
Chemical structure
MeC(OMe)3, Pyr.TsOH
CH2Cl2
Chemical structure
TMSCl
Chemical structure
+
Chemical structure
K2CO3
MeOH
96% (3 steps)
Chemical structure
i-Bu2AlH
PhMe
Chemical structure
DMF
160 °C, 66% (2 steps)
Chemical structure

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