Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorMartin E. Kuehne
Publication year1998
Synthesis typeTotal
Number of steps 21 (linear)
References
Part 1 of 1
intermediate structure
PhCHO, MgSO4, NaBH4
MeOH
0 °C to RT, 6 h
intermediate structure
Boc2O, Et3N
CH2Cl2
RT, ON, 89% (2 steps)
intermediate structure + intermediate structure
t-BuOCl, Et3N, ZnCl2
THF
-78 °C to RT, ON
intermediate structure
LiCl
DMF
135 °C, 4 h, 88% (2 steps)
intermediate structure
TMSOTf, Et3N
CH2Cl2
0 °C to RT, 60 min, 97%
intermediate structure + intermediate structure
BzOH, Hydroquinone
PhH
Reflux, 10 h, 84%
intermediate structure
NH3
MeOH
0 °C to RT, 5 d, 87%
"The yield was 95 % brsm."
intermediate structure
(CF3CO)2O, i-Pr2NEt
CH2Cl2
0 °C to RT, 40 min
intermediate structure
KBH4
EtOH
75 °C, 4 h, 76% (2 steps)
intermediate structure
K2OsO2(OH)4, KIO4
THF, H2O
0 °C, 4 h, 62%
intermediate structure + intermediate structure
n-BuLi
THF
-78 °C, 4.5 h, 73%
intermediate structure
NCS, Me2S, Et3N
PhMe
-20 °C to RT, 80 min, 94%
intermediate structure
TsOH
THF, H2O
RT, 2 h, 82%
intermediate structure
Ts2O, Et3N, DMAP
DCE, MeOH
0 to 60 °C, 2 h
intermediate structure
H2, PdCl2
MeOH
RT, 3 h, 91% (2 steps)
intermediate structure
(EtO)2P(O)CH2CO2Me, TMS2NK
THF
0 °C to RT, 8.5 h, 64%
intermediate structure
i-Bu2AlH, BF3.OEt2
CH2Cl2
-78 °C, 3.5 h, 91%
intermediate structure
NaBH3CN
AcOH
10 °C, 30 min
intermediate structure
NaOMe
MeOH
RT, 2 h, 92% (2 steps)
intermediate structure
i-Bu2AlH
CH2Cl2
-90 °C, 30 min, 71%
intermediate structure
Malonic Acid, NaOAc
AcOH, Ac2O
110 °C, , 65%
See the Aldol Addition
intermediate structure