Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorChristopher D. Vanderwal
Publication year2011
Synthesis typeFormal
Number of steps 9 (3 parts)
References
Part 1 of 3
intermediate structure
AllylNH2
RT, 44 h, 100%
intermediate structure + intermediate structure
EtOH
RT to 80 °C, 3.5 h, 81%
See the Zincke Reaction
"The yield was 100 % brsm."
intermediate structure
KOt-Bu
THF
80 °C, 3.5 h, 64%
intermediate structure
Part 2 of 3
intermediate structure
Me2SiH(OEt), [Cp*Ru(MeCN)3]PF6
Acetone
0 °C to RT, 2.5 h
intermediate structure
MsCl, Et3N, LiBr
THF
-25 °C to RT, 5 h
intermediate structure
MeMgBr
Et2O
-78 °C, 35 min, 47% (3 steps)
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
Pd(PPh3)4, i-Pr2NEt
CHCl3, MeCN
0 °C, 3.5 h, 69%
intermediate structure
TMS2NNa, CuBr.Me2S
NMP
0 to 65 °C, 95 min, 10%
intermediate structure
Remaining...
70% (1 step)
"See: Chem. Ind. 1953, 245."
intermediate structure