Synthesis of Strychnine
C21H22N2O2
| Principal investigator | Rodrigo B. Andrade |
|---|---|
| Publication year | 2010 |
| Synthesis type | Total |
| Number of steps | 15 (linear) |
| References |
Part 1 of 1
+
+
+
BnNH2,
MgSO4
CH2Cl2
RT, 16 h
+
+
2,6-Di-tert-butyl-4-methylpyridine,
DBU,
AgOTf
PhMe
RT, 13.5 h, 70%
See the Friedel-Crafts Alkylation
See the Morita-Baylis-Hillman Reaction
PhMe
110 °C, 60 min, 81%
Et3O+ BF4-
CH2Cl2
0 °C to RT, 110 min
NaBH4
MeOH
0 °C to RT, 2 h, 74% (2 steps)
Proton Sponge,
ClCO2CH(Cl)CH3
DCE
0 to 90 °C, 16 h
ClCO2CH(Cl)CH3
135 °C, 48 h
MeOH
Reflux, 3 h, 75% (3 steps)
+
K2CO3
MeCN
0 °C, 16 h, 63%
NaBH3CN
AcOH
10 °C, 60 min
NaOMe
MeOH, THF
RT, 5 h, 80% (2 steps)
i-Bu2AlH
CH2Cl2
-78 °C, 60 min