Synthesis of Strychnine

C21H22N2O2
Principal investigator | Rodrigo B. Andrade |
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Publication year | 2010 |
Synthesis type | Total |
Number of steps | 15 (linear) |
References |
Part 1 of 1
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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

