Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorHans-Ulrich Reissig
Publication year2010
Synthesis typeFormal
Number of steps 9 (linear)
References
Angew. Chem. Int. Ed. 2010, 49, 8021.
Part 1 of 1
intermediate structure + intermediate structure
DMAP, Et3N
CH2Cl2
RT, 3 d, 82%
intermediate structure
BrCH2CN, SmI2
HMPA, THF
RT, ON, 77%
intermediate structure
Ni (Raney), H2
1 atm
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
n-Bu4N+ I-, K2CO3
MeCN
RT, ON, 65% (2 steps)
intermediate structure
Pd(OAc)2, K2CO3, n-Bu4N+ Cl-
DMF
70 °C, 4 h, 68%
See the Mizoroki-Heck Reaction
intermediate structure
Report an error in this part
Remaining...
27% (2 steps)
"See : J. Org. Chem. 1994, 59, 2685; J. Org. Chem. 1993, 58, 7490."
intermediate structure