Synthesis of Strychnine

C21H22N2O2
Principal investigator | Miwako Mori |
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Publication year | 2002 |
Synthesis type | Total |
Number of steps | 22 (linear) |
References |
Part 1 of 1
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HCl
H2O, THF
RT, 60 min, 100%

PBr3
THF
0 °C to RT, 90 min, 90%

NaCN
DMSO
RT, 60 min, 95%

Me2PPh,
Ag2CO3,
Pd(OAc)2
DMSO
90 °C, 17 h, 87%
See the Mizoroki-Heck Reaction
"Cristallized to >99:01 er (73 % yield)."

LiAlH4
THF
0 °C to RT, 90 min

Et3N,
Boc2O
DMF
RT, 60 min, 66% (2 steps)

Pd(OAc)2,
MnO2,
Hydroquinone
AcOH
RT to 50 °C, 20.5 h, 77%

- 9-BBN
- NaOH , H2O2 , H2O
THF
0 to 50 °C, 13 h, 80%
"Also isolated was the regioisomer (5 % yield)."


PhNTf2,
TMS2NK
THF
-35 °C to RT, 15 min, 63%

Pd(OAc)2,
i-Pr2NEt,
HCO2H,
Ph3P
DMF
60 °C, 60 min, 100%

Na.Naphthalene
THF
-78 to 0 °C, 15 min, 89%


K2CO3
THF
0 °C, 30 min, 66%


NaOi-Pr
i-PrOH
RT, 60 min, 81%

CF3CO2H
CH2Cl2
0 °C, 30 min


Li2CO3
DMF
40 °C, 14 h, 66% (2 steps)


LiAlH4
THF
0 °C, 25 min, 47%

HCl
H2O, THF
RT, 3 h, 96%

KOH
EtOH, H2O
Reflux, 6 h, 16%
