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Named reactions

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Search synthesis

Strychnine

Chemical structure of Strychnine
C21H22N2O2
Author Robert B. Woodward
Publication year 1954
Synthesis type Total synthesis
Number of steps 29 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
PPA
100 °C, 10 min, 54%

See the Fischer Indole Synthesis
Chemical structure
CH2O, Me2NH, AcOH
Dioxane , H2O
RT, 2 h, 92%

See the Friedel-Crafts Alkylation
Chemical structure
MeI
PhH
0 °C, 2 h
Chemical structure
NaCN
DMF
Reflux, 60 min, 97% (2 steps)
Chemical structure
LiAlH4
THF
RT to Reflux, 3 h, 85%
Chemical structure
Ethyl glyoxalate
Dean-Stark
PhH
Reflux, 5 h, 92%
Chemical structure
TsCl
Pyr
RT, 18 h, 64%
Chemical structure
NaBH4
EtOH, H2O
RT, 60 min, 85%
Chemical structure
Ac2O
Pyr
100 °C, 60 min, 99%
Chemical structure
O3
AcOH, H2O
RT, 22 min, 29%
Chemical structure
HCl
MeOH
Reflux, 10 h, 75%
Chemical structure
HI, P (Red)
AcOH, H2O
Reflux, 3.5 h, 72%
Chemical structure
Ac2O
Pyr
RT, 60 min, 94%
Chemical structure
CH2N2
MeOH
RT, 60 min, 84%
Chemical structure
NaOMe
MeOH
Reflux, 20 min, 88%

See the Dieckmann Condensation
Chemical structure
TsCl
Pyr
RT, 10 h, 95%
Chemical structure
NaSBn
MeOH
RT, 3 h, 77%

See the Michael Addition
Chemical structure
Ni (Raney)
EtOH
Reflux, 3 h, 84%
Chemical structure
H2, Pd/C
EtOH
RT, 2 min, 73%
Chemical structure
KOH
MeOH, H2O
Reflux, 60 min, 59%

The yield was 82 % brsm. The enantiomers were resolved by crystallization with (-)-quinine (21 % yield).
Chemical structure
Ac2O
Pyr
Reflux, 60 min, 42%

See the Dakin-West Reaction
Chemical structure
HCl
H2O, AcOH
Reflux, 6 h
Chemical structure
SeO2
EtOH
RT to Reflux, 16 h, 12% (2 steps)
Chemical structure
Sodium acetylide
THF
0 °C to RT, 60 min, 53%
Chemical structure
H2, Lindlar Catalyst
MeOH
RT, 3 min, 86%
Chemical structure
LiAlH4
Et2O, THF
Reflux, 30%
Chemical structure
HBr, P (Red)
AcOH
120 °C, 3.5 h
Chemical structure
H2SO4
H2O
Reflux, 90 min, 13% (2 steps)

Also isolated was an oil which, once treated with acetic anhydride and pyridine, afforded a mixture of isostrychnine acetates.
Chemical structure
KOH
EtOH
100 °C, 5 h

See the Michael Addition
8 mg of strychnine was obtained from a mixture of 7 mg isostrychnine and 65 mg isostrychnine acetates.
Chemical structure

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