Synthesis of Strychnine
C21H22N2O2
Principal investigator | Viresh H. Rawal |
---|---|
Publication year | 1994 |
Synthesis type | Formal |
Number of steps | 15 (3 parts) |
References |
Part 1 of 3
NaOH,
Br(CH2)2Br,
n-Bu4N+ Br-
H2O, MeCN
RT
i-Bu2AlH
PhMe
-78 °C, 96% (2 steps)
MgSO4,
BnNH2
Et2O
RT
NaI,
TMSCl
DMF
60 °C, 96% (2 steps)
ClCO2Me
Acetone
RT
Pd/C,
HCO2NH4
MeOH
RT, 86% (2 steps)
Part 2 of 3
NaBH4,
n-Bu3SnCl,
Methyl acrylate
hν
EtOH
70%
H2Cr2O7.2Pyr,
Celite
CH2Cl2
RT, 89%
Part 3 of 3
+
+
ClCO2Me,
PhNEt2
RT, 85%
TMSI
CHCl3, MeOH
Reflux, 11 h, 91%
K2CO3
Acetone, DMF
82%
HCl
H2O, THF
96%
Remaining...
28% (1 step)
"The yield was 72 % brsm. See : J. Org. Chem. 1993, 58, 7490."