Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorRodrigo B. Andrade
Publication year2010
Synthesis typeTotal
Number of steps 15 (linear)
References
Part 1 of 1
intermediate structure
BnNH2, MgSO4
CH2Cl2
RT, 16 h
intermediate structure + intermediate structure + intermediate structure
CF3CO2H
CH2Cl2
-78 °C to RT, 5.5 h, 78%
intermediate structure
AgOTf, 2,6-Di-tert-butyl-4-methylpyridine, DBU
PhMe
RT, 13.5 h, 70%
intermediate structure
PhMe
110 °C, 60 min, 81%
intermediate structure
Et3O+ BF4-
CH2Cl2
0 °C to RT, 110 min
intermediate structure
NaBH4
MeOH
0 °C to RT, 2 h, 74% (2 steps)
intermediate structure
ClCO2CH(Cl)CH3, Proton Sponge
DCE
0 to 90 °C, 16 h
intermediate structure
ClCO2CH(Cl)CH3
135 °C, 48 h
intermediate structure
MeOH
Reflux, 3 h, 75% (3 steps)
intermediate structure + intermediate structure
K2CO3
MeCN
0 °C, 16 h, 63%
intermediate structure
Pd(OAc)2, Ph3P
Et3N
90 °C, 2 h, 85%
See the Heck Coupling
intermediate structure
NaBH3CN
AcOH
10 °C, 60 min
intermediate structure
NaOMe
MeOH, THF
RT, 5 h, 80% (2 steps)
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 60 min
intermediate structure
Malonic Acid, NaOAc
AcOH, Ac2O
110 °C, 2 h, 49% (2 steps)
See the Aldol Addition
intermediate structure