Synthesis of Strychnine

C21H22N2O2
Principal investigator | Martin E. Kuehne |
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Publication year | 1993 |
Synthesis type | Total |
Number of steps | 19 (linear) |
References |
Part 1 of 1
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BnBr,
K2CO3
MeOH
Reflux, 3 d, 89%

t-BuOCl,
Et3N
THF
-78 °C, 2.5 h




H2,
Pd/C
1 atm
AcOH
RT, 87%



HClO4
H2O, THF
0 °C to RT, 5 h, 51% (2 steps)


- DBU
- H2 , Pd/C
1 atm
MeOH
RT to Reflux, 12 h, 70% (2 steps)

NaBH3CN
AcOH
RT, 30 min

Ac2O
Pyr
RT, 10 h, 83% (2 steps)


NaBH4
AcOH, MeOH
0 °C, 60 min, 64% (2 steps)

Ac2O
Pyr
RT, ON, 98%

DBU
Dioxane , H2O
Reflux, 10 h, 61%


TMS2NK,
(EtO)2P(O)CH2CO2Me
THF
RT, 2.5 h, 39%
See the Horner-Wadsworth-Emmons Reaction
"Also isolated was the Z-isomer (42 % yield) which could be photoisomerized to the desired product."

BF3.OEt2,
i-Bu2AlH
CH2Cl2
-78 °C, 4.5 h, 87%

KOH
EtOH
Reflux, 6 h, 28%
"The yield was 72 % brsm."
