Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorDavid W. C. MacMillan
Publication year2011
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
NaH, (4-MeOPh)CH2Cl
DMF
0 °C to RT, 35 min, 94%
intermediate structure
SeO2
Dioxane , H2O
100 °C, 5 h, 87%
intermediate structure
TMS2NK, 18-Crown-6, (EtO)2P(O)CH2SeMe
THF
-78 °C to RT, 90 min, 81%
intermediate structure + intermediate structure
Br3CCO2H
PhMe
-60 °C to RT, 23 h, 82%
intermediate structure
(Ph3P)3RhCl
PhMe, PhCN
120 °C, 5.5 h, 86%
intermediate structure
Phosgene, Et3N, MeOH
PhMe
-45 °C to RT, 3 h, 88%
intermediate structure
i-Bu2AlH, CF3CO2H
CH2Cl2, MeOH
-78 °C to RT, 3 h, 81%
intermediate structure + intermediate structure
DBU, K2CO3
DMF
RT, 50 min, 84%
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h, 91%
intermediate structure
NaHCO3, Pd(OAc)2, n-Bu4N+ Cl-
EtOAc
RT, 24 h, 58%
See the Heck Coupling
intermediate structure
PhSH
CF3CO2H
45 °C, 13 h, 66%
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
120 °C, 2 h, 69%
See the Aldol Addition
intermediate structure