Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorAlbert Padwa
Publication year2007
Synthesis typeTotal
Number of steps 17 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
n-BuLi
THF
0 °C, 40 min, 68%
intermediate structure
AcCl, NaOH, n-Bu4N+ HSO4-
CH2Cl2
0 °C to RT, 35 min, 88%
intermediate structure
Mg(ClO4)2
MeCN
45 °C, 90 min, 77%
intermediate structure + intermediate structure
NaH
DMF
0 °C, 5 h, 84%
intermediate structure
MgI2
PhMe
150 °C, 3 h, 95%
intermediate structure
NaBH4
EtOH, THF
0 °C, 30 min
intermediate structure
NaOMe
MeOH, THF
RT, 15 min
intermediate structure
LiAlH4
THF
Reflux, 3 h
intermediate structure
NaBH(OAc)3
DCE
-20 °C, 3 h, 65% (4 steps)
intermediate structure
H2, Pd(OH)2/C
MeOH
RT, 2 d, 70%
intermediate structure + intermediate structure
K2CO3
DMF, H2O
0 °C, 12 h, 80%
intermediate structure
3,5-Dimethoxybenzaldehyde, NaBH(OAc)3
DCE, AcOH
0 °C to RT, 12 h, 86%
intermediate structure
n-Pr4N+ RuO4-, NMO
MeCN
0 °C to RT, 2.5 h, 80%
intermediate structure
Pd(PPh3)4, KOPh
THF
Reflux, 2 h, 56%
intermediate structure
Ph2P(O)CH2OMe, i-Pr2NLi
THF
0 °C to RT, 25 h, 72%
intermediate structure
HCl
THF, H2O
55 °C, 10 h
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
120 °C, 2 h, 43% (2 steps)
intermediate structure