Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorGraham J. Bodwell
Publication year2002
Synthesis typeFormal
Number of steps 9 (linear)
References
Angew. Chem. Int. Ed. 2002, 41, 3261.
Part 1 of 1
intermediate structure + intermediate structure
s-BuOH
Reflux, 4 d, 100%
intermediate structure
KOH, AllylBr
DMF
RT, 3 h, 91%
intermediate structure
  1. 9-BBN
  2. Cs2CO3 , Pd(PPh3)4 , H2O
THF
0 °C to reflux, 60 h, 65%
See the Suzuki Coupling
intermediate structure
TMS2NNa, ClCO2Me
THF
-78 °C to RT, 4 h, 96%
intermediate structure
PhNEt2
Reflux, 60 min, 100%
See the Diels-Alder Reaction
intermediate structure
NaBH4
PhH, CF3CO2H
0 °C to RT, 12 h, 100%
intermediate structure
Celite, H2Cr2O7.2Pyr
CH2Cl2
RT, 3 d, 30%
intermediate structure
TMSI
CHCl3
Reflux, 6 h, 100%
intermediate structure
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Remaining...
16% (4 steps)
"See : J. Org. Chem. 1994, 59, 2685; J. Org. Chem. 1993, 58, 7490."
intermediate structure