Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorHans-Ulrich Reissig
Publication year2010
Synthesis typeFormal
Number of steps 9 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Et3N, DMAP
CH2Cl2
RT, 3 d, 82%
intermediate structure
SmI2, BrCH2CN
THF, HMPA
RT, ON, 77%
intermediate structure
H2, Ni (Raney)
MeOH
RT, 3 d, 97%
intermediate structure
ClCO2Me, Et3N, DMAP
CH2Cl2
RT, 4 h, 87%
intermediate structure
MsCl, Et3N, DMAP, DBU
CH2Cl2
RT, 48 h, 63%
intermediate structure
TMSI
CHCl3
Reflux, 2 h
intermediate structure + intermediate structure
K2CO3, n-Bu4N+ I-
MeCN
RT, ON, 65% (2 steps)
intermediate structure
Pd(OAc)2, K2CO3, n-Bu4N+ Cl-
DMF
70 °C, 4 h, 68%
See the Heck Coupling
intermediate structure
Remaining...
27% (2 steps)
"See : J. Org. Chem. 1994, 59, 2685; J. Org. Chem. 1993, 58, 7490."
intermediate structure