Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorStephen F. Martin
Publication year2001
Synthesis typeFormal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure + intermediate structure
THF
-78 °C to RT, 2 h, 79%
intermediate structure
Mesitylene
160 °C, 72 h, 85%
intermediate structure
HClO4
THF, H2O
80 °C, 12 h, 93%
intermediate structure
(Ph3P)3RuCl2
PhMe
Reflux, 24 h, 79%
intermediate structure
H2, Pd(OH)2/C
EtOAc, EtOH
RT, 5 h, 67%
intermediate structure
NaOMe, TsOH
MeOH
0 °C to RT, 30 h, 74%
intermediate structure
TBSCl, DMAP
Pyr
RT, 24 h, 71%
intermediate structure
Me3O+BF4-, 2,6-Di-tert-butylpyridine
MeOH
RT, 24.5 h, 83%
intermediate structure
t-BuOCl, SnCl4
PhMe
-15 °C, 60 min
intermediate structure
TMS2NLi
THF
-15 °C to RT, 3.5 h, 26%
intermediate structure
HCl
MeOH, H2O
RT, ON, 83%
intermediate structure
Remaining...
34% (4 steps)
"See: J. Am. Chem. Soc. 1993, 115, 9293."
intermediate structure