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Named reactions

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Strychnine

Chemical structure of Strychnine
C21H22N2O2
Author Tohru Fukuyama
Publication year 2004
Synthesis type Total synthesis
Number of steps 29 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
CSCl2, Na2CO3
THF, H2O
-10 °C, 30 min, 56%
Chemical structure
TBSCl, Imidazole
CH2Cl2
RT, 5 min, 98%
Chemical structure
Dimethyl malonate, NaH
THF
0 °C to RT, 100 min, 71%
Chemical structure
n-Bu3SnH, Et3B
PhMe
RT, 10 min, 52%

See the Fukuyama Indole Synthesis
Chemical structure

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Part 2 of 3
Chemical structure
Na
NH3, EtOH
-78 °C

See the Birch Reduction
Chemical structure
AcCl, HC(OMe)3, NaOMe
MeOH
0 °C to RT, 22 h
Chemical structure
NBS
DMSO, H2O
RT, 10 min, 62% (3 steps)
Chemical structure
Lipase AYS, VinylOAc
40 °C, 12 h, 46%

Selectivity : >99:01 er
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 5 min, 73%
Chemical structure
NaOMe
MeOH
RT, 5 min
Chemical structure
TBSCl, Imidazole
CH2Cl2
RT, 5 min, 61% (2 steps)
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Pd2(dba)3, (2-Furyl)3P
PhMe
RT, 20 min, 86%

See the Tsuji-Trost Reaction
Chemical structure
MeOCH2Cl, i-Pr2NEt
CH2Cl2
RT, 3 h
Chemical structure
LiI, 2,4,6-Collidine
80 °C, 60 min

See the Krapcho Decarboxylation
Chemical structure
Boc2O, DMAP
MeCN
RT, 20 min
Chemical structure
HF, NH4F
DMF, NMP
RT, 19 h, 72% (4 steps)
Chemical structure
NsNH2, Ph3P, DEAD
PhMe
RT, 5 min, 95%

See the Mitsunobu Reaction
Chemical structure
DBU
PhMe
100 °C, 3 h
Chemical structure
HCl
THF, H2O
50 °C, 2.5 h
Chemical structure
Dess-Martin Periodinane
CH2Cl2
0 °C to RT, 35 min, 69% (3 steps)

See the Dess-Martin Oxidation
Chemical structure
TMSOTf, Et3N
CH2Cl2
0 °C, 10 min
Chemical structure
mCPBA, NaHCO3
CH2Cl2, H2O
0 °C, 66% (2 steps)

See the Rubottom Oxidation
Chemical structure
Pb(OAc)4
MeOH, PhH
0 °C, 10 min

See the Criegee Reaction
Chemical structure
PhSH, Cs2CO3, Me2S, CF3CO2H
CH2Cl2
RT to 50 °C, 7.5 h, 84% (2 steps)

See the Pictet-Spengler Reaction
Chemical structure
i-Bu2AlH, BF3.OEt2
CH2Cl2
-78 °C, 70 min, 93%
Chemical structure
NaBH3CN
AcOH
10 °C, 60 min
Chemical structure
NaOMe
MeOH
RT, 7.5 h
Chemical structure
i-Bu2AlH
CH2Cl2
-98 °C
Chemical structure
Malonic Acid, NaOAc
AcOH, Ac2O
110 °C, 2 h, 42% (4 steps)

See the Aldol Addition
Chemical structure

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