Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorMiwako Mori
Publication year2002
Synthesis typeTotal
Number of steps 22 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Pd2(dba)3.CHCl3
DMF
0 °C, 36 h, 80%
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
Pd(OAc)2, Ag2CO3, Me2PPh
DMSO
90 °C, 17 h, 87%
See the Heck Coupling
"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. H2O
  2. H2O2
  3. NaOH
  4. 9-BBN
THF
0 to 50 °C, 13 h, 80%
"Also isolated was the regioisomer (5 % yield)."
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 85 min, 87%
See the Swern Oxidation
intermediate structure
TMS2NK, PhNTf2
THF
-35 °C to RT, 15 min, 63%
intermediate structure
HCO2H, i-Pr2NEt, Pd(OAc)2, 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
i-Pr2NEt, Pd(OAc)2, Ph3P
DMSO
80 °C, 90 min, 46%
See the Heck Coupling
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
K2CO3, Pd(OAc)2, Ph3P, n-Bu4N+ Cl-
DMF
70 °C, 30 min, 48%
See the Heck Coupling
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