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Named reactions

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Strychnine

Chemical structure of Strychnine
C21H22N2O2
Author Miwako Mori
Publication year 2002
Synthesis type Total synthesis
Number of steps 22 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
Reagent structure
Pd2(dba)3.CHCl3
DMF
0 °C, 36 h, 80%

Selectivity : 92:08 er
See the Tsuji-Trost Reaction
Chemical structure
HCl
THF, H2O
RT, 60 min, 100%
Chemical structure
PBr3
THF
0 °C to RT, 90 min, 90%
Chemical structure
NaCN
DMSO
RT, 60 min, 95%
Chemical structure
Pd(OAc)2, Me2PPh, Ag2CO3
DMSO
90 °C, 17 h, 87%

See the Heck Coupling
Cristallized to >99:01 er (73 % yield).
Chemical structure
LiAlH4
THF
0 °C to RT, 90 min
Chemical structure
Boc2O, Et3N
DMF
RT, 60 min, 66% (2 steps)
Chemical structure
Pd(OAc)2, Hydroquinone, MnO2
AcOH
RT to 50 °C, 20.5 h, 77%
Chemical structure
  1. 9-BBN
  2. H2O2, NaOH, H2O
THF
0 to 50 °C, 13 h, 80%

Also isolated was the regioisomer (5 % yield).
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 85 min, 87%

See the Swern Oxidation
Chemical structure
PhNTf2, TMS2NK
THF
-35 °C to RT, 15 min, 63%
Chemical structure
Pd(OAc)2, Ph3P, i-Pr2NEt, HCO2H
DMF
60 °C, 60 min, 100%
Chemical structure
Na.Naphthalene
THF
-78 to 0 °C, 15 min, 89%
Chemical structure + Chemical structure
K2CO3
THF
0 °C, 30 min, 66%
Chemical structure
Pd(OAc)2, Ph3P, i-Pr2NEt
DMSO
80 °C, 90 min, 46%

See the Heck Coupling
Chemical structure
NaOi-Pr
i-PrOH
RT, 60 min, 81%
Chemical structure
CF3CO2H
CH2Cl2
0 °C, 30 min
Chemical structure + Chemical structure
Li2CO3
DMF
40 °C, 14 h, 66% (2 steps)
Chemical structure
Pd(OAc)2, Ph3P, n-Bu4N+ Cl-, K2CO3
DMF
70 °C, 30 min, 48%

See the Heck Coupling
Chemical structure
LiAlH4
THF
0 °C, 25 min, 47%
Chemical structure
HCl
THF, H2O
RT, 3 h, 96%
Chemical structure
KOH
EtOH, H2O
Reflux, 6 h, 16%
Chemical structure

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