Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorViresh H. Rawal
Publication year1994
Synthesis typeFormal
Number of steps 15 (3 parts)
References
Part 1 of 3
intermediate structure
Br(CH2)2Br, NaOH, n-Bu4N+ Br-
MeCN, H2O
RT
intermediate structure
i-Bu2AlH
PhMe
-78 °C, , 96% (2 steps)
intermediate structure
BnNH2, MgSO4
Et2O
RT
intermediate structure
TMSCl, NaI
DMF
60 °C, , 96% (2 steps)
intermediate structure
ClCO2Me
Acetone
RT
intermediate structure
HCO2NH4, Pd/C
MeOH
RT, , 86% (2 steps)
intermediate structure
Part 2 of 3
intermediate structure
Methyl acrylate, n-Bu3SnCl, NaBH4
EtOH
70%
intermediate structure
H2Cr2O7.2Pyr, Celite
CH2Cl2
RT, , 89%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
ClCO2Me, PhNEt2
RT, , 85%
intermediate structure
PhH
185-200 °C, 4 h, 99%
intermediate structure
TMSI
CHCl3, MeOH
Reflux, 11 h, 91%
intermediate structure + intermediate structure
K2CO3
Acetone, DMF
82%
intermediate structure
Pd(OAc)2, K2CO3, n-Bu4N+ Cl-
DMF
70 °C, 3 h, 74%
See the Heck Coupling
intermediate structure
HCl
THF, H2O
96%
intermediate structure
Remaining...
28% (1 step)
"The yield was 72 % brsm. See : J. Org. Chem. 1993, 58, 7490."
intermediate structure