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Named reactions

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Search synthesis

Strychnine

Chemical structure of Strychnine
C21H22N2O2
Author Martin E. Kuehne
Publication year 1998
Synthesis type Total synthesis
Number of steps 21 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
PhCHO, MgSO4, NaBH4
MeOH
0 °C to RT, 6 h
Chemical structure
Boc2O, Et3N
CH2Cl2
RT, ON, 89% (2 steps)
Chemical structure + Chemical structure
t-BuOCl, Et3N, ZnCl2
THF
-78 °C to RT, ON

See the Mannich Reaction
Chemical structure
LiCl
DMF
135 °C, 4 h, 88% (2 steps)

See the Krapcho Decarboxylation
Chemical structure
TMSOTf, Et3N
CH2Cl2
0 °C to RT, 60 min, 97%
Chemical structure + Chemical structure
BzOH, Hydroquinone
Dean-Stark
PhH
Reflux, 10 h, 84%

See the Pictet-Spengler Reaction
Chemical structure
NH3
MeOH
0 °C to RT, 5 d, 87%

The yield was 95 % brsm.
Chemical structure
(CF3CO)2O, i-Pr2NEt
CH2Cl2
0 °C to RT, 40 min
Chemical structure
KBH4
EtOH
75 °C, 4 h, 76% (2 steps)
Chemical structure
K2OsO2(OH)4, KIO4
THF, H2O
0 °C, 4 h, 62%

See the Lemieux-Johnson Oxidation
Chemical structure + Chemical structure
n-BuLi
THF
-78 °C, 4.5 h, 73%
Chemical structure
NCS, Me2S, Et3N
PhMe
-20 °C to RT, 80 min, 94%

See the Corey-Kim Oxidation
Chemical structure
TsOH
THF, H2O
RT, 2 h, 82%
Chemical structure
Ts2O, Et3N, DMAP
DCE, MeOH
0 to 60 °C, 2 h
Chemical structure
H2, PdCl2
1 atm
MeOH
RT, 3 h, 91% (2 steps)
Chemical structure
(EtO)2P(O)CH2CO2Me, TMS2NK
THF
0 °C to RT, 8.5 h, 64%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
i-Bu2AlH, BF3.OEt2
CH2Cl2
-78 °C, 3.5 h, 91%
Chemical structure
NaBH3CN
AcOH
10 °C, 30 min
Chemical structure
NaOMe
MeOH
RT, 2 h, 92% (2 steps)
Chemical structure
i-Bu2AlH
CH2Cl2
-90 °C, 30 min, 71%
Chemical structure
Malonic Acid, NaOAc
AcOH, Ac2O
110 °C, 65%

See the Aldol Addition
Chemical structure

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