Synthesis of Strychnine

C21H22N2O2
Principal investigator | Albert Padwa |
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Publication year | 2007 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1
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n-BuLi
THF
0 °C, 40 min, 68%

AcCl,
NaOH,
n-Bu4N+ HSO4-
CH2Cl2
0 °C to RT, 35 min, 88%

Mg(ClO4)2
MeCN
45 °C, 90 min, 77%


NaH
DMF
0 °C, 5 h, 84%


NaBH4
EtOH, THF
0 °C, 30 min

NaOMe
MeOH, THF
RT, 15 min

LiAlH4
THF
Reflux, 3 h

NaBH(OAc)3
DCE
-20 °C, 3 h, 65% (4 steps)

Pd(OH)2/C,
H2
4 atm
MeOH
RT, 2 d, 70%


K2CO3
DMF, H2O
0 °C, 12 h, 80%

NaBH(OAc)3,
3,5-Dimethoxybenzaldehyde
AcOH, DCE
0 °C to RT, 12 h, 86%


Pd(PPh3)4,
KOPh
THF
Reflux, 2 h, 56%


HCl
H2O, THF
55 °C, 10 h

Malonic Acid,
NaOAc
Ac2O, AcOH
120 °C, 2 h, 43% (2 steps)
