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Named reactions

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Search synthesis

Quinine

Chemical structure of Quinine
C20H24N2O2
Author Gilbert Stork
Publication year 2001
Synthesis type Total synthesis
Number of steps 17 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Et2NH, AlMe3
CH2Cl2
0 °C to RT, ON, 82%
Chemical structure
TBSCl, Imidazole
CH2Cl2
RT, 18 h, 97%
Chemical structure + Chemical structure
i-Pr2NLi
THF
-78 °C to RT, 5 h, 79%
Chemical structure
Pyr.TsOH
EtOH
RT, ON, 93%
Chemical structure
Xylene(s)
Reflux, 12 h, 97%
Chemical structure
i-Bu2AlH
THF
-78 °C, 5 h
Chemical structure
Ph3P+CH2OMe Cl-, TMS2NK
THF
-78 °C to RT, ON, 75% (2 steps)

See the Wittig Reaction
Chemical structure
(PhO)2P(O)N3, Ph3P, DEAD
THF
0 °C, 24 h, 95%

See the Mitsunobu Reaction
Chemical structure
HCl
CH2Cl2, THF, H2O
RT, 8 h, 78%
Chemical structure + Chemical structure
i-Pr2NLi
THF
-78 to 0 °C, 65 min, 72%
Chemical structure
DMSO, (COCl)2, Et3N
CH2Cl2
-78 °C to RT, 90 min, 85%

See the Swern Oxidation
Chemical structure
Ph3P
THF
Reflux, 3 h, 81%

See the Wittig Reaction
Chemical structure
NaBH4
THF, MeOH
RT, 3 h, 91%
Chemical structure
HF
MeCN, H2O
RT, 60 min, 95%
Chemical structure
MsCl, Pyr
CH2Cl2
RT, ON
Chemical structure
MeCN
Reflux, 3 h, 68% (2 steps)
Chemical structure
O2, NaH
DMSO
70 °C, 45 min, 78%
Chemical structure

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