Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorMiwako Mori
Publication year2002
Synthesis typeTotal
Number of steps 22 (linear)
References
Angew. Chem. Int. Ed. 2002, 41, 1934. J. Am. Chem. Soc. 2003, 125, 9801.
Part 1 of 1
intermediate structure + intermediate structure
Special reagent
Pd2(dba)3.CHCl3
DMF
0 °C, 36 h, 80%
See the Tsuji-Trost Reaction
intermediate structure
HCl
H2O, THF
RT, 60 min, 100%
intermediate structure
PBr3
THF
0 °C to RT, 90 min, 90%
intermediate structure
NaCN
DMSO
RT, 60 min, 95%
intermediate structure
Me2PPh, Ag2CO3, Pd(OAc)2
DMSO
90 °C, 17 h, 87%
See the Mizoroki-Heck Reaction
"Cristallized to >99:01 er (73 % yield)."
intermediate structure
LiAlH4
THF
0 °C to RT, 90 min
intermediate structure
Et3N, Boc2O
DMF
RT, 60 min, 66% (2 steps)
intermediate structure
Pd(OAc)2, MnO2, Hydroquinone
AcOH
RT to 50 °C, 20.5 h, 77%
intermediate structure
  1. 9-BBN
  2. NaOH , H2O2 , H2O
THF
0 to 50 °C, 13 h, 80%
"Also isolated was the regioisomer (5 % yield)."
intermediate structure
Et3N, DMSO, (COCl)2
CH2Cl2
-78 °C to RT, 85 min, 87%
See the Swern Oxidation
intermediate structure
PhNTf2, TMS2NK
THF
-35 °C to RT, 15 min, 63%
intermediate structure
Pd(OAc)2, i-Pr2NEt, HCO2H, Ph3P
DMF
60 °C, 60 min, 100%
intermediate structure
Na.Naphthalene
THF
-78 to 0 °C, 15 min, 89%
intermediate structure + intermediate structure
K2CO3
THF
0 °C, 30 min, 66%
intermediate structure
Pd(OAc)2, i-Pr2NEt, Ph3P
DMSO
80 °C, 90 min, 46%
See the Mizoroki-Heck Reaction
intermediate structure
NaOi-Pr
i-PrOH
RT, 60 min, 81%
intermediate structure
CF3CO2H
CH2Cl2
0 °C, 30 min
intermediate structure + intermediate structure
Li2CO3
DMF
40 °C, 14 h, 66% (2 steps)
intermediate structure
n-Bu4N+ Cl-, Ph3P, Pd(OAc)2, K2CO3
DMF
70 °C, 30 min, 48%
See the Mizoroki-Heck Reaction
intermediate structure
LiAlH4
THF
0 °C, 25 min, 47%
intermediate structure
HCl
H2O, THF
RT, 3 h, 96%
intermediate structure
KOH
EtOH, H2O
Reflux, 6 h, 16%
intermediate structure
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