Join us on Facebook
Follow us on Twitter
Subscribe to our RSS Feed
Strychnine
"Dedicated to my colleague and friend David Goldsmith on the occasion of his 75th birthday."
| Author | Albert Padwa |
|---|---|
| Publication year | 2007 |
| Synthesis type | Total synthesis |
| Number of steps | 17 (linear) |
| References |
Browse hundreds of other total syntheses.
Part 1 of 1
+ 
n-BuLi
THF
0 °C, 40 min, 68 %
0 °C, 40 min, 68 %
AcCl, NaOH, n-Bu4N+ HSO4-
CH2Cl2
0 °C to RT, 35 min, 88 %
0 °C to RT, 35 min, 88 %
Mg(ClO4)2
MeCN
45 °C, 90 min, 77 %
45 °C, 90 min, 77 %
+ 
NaH
DMF
0 °C, 5 h, 84 %
0 °C, 5 h, 84 %
NaBH4
EtOH, THF
0 °C, 30 min
0 °C, 30 min
NaOMe
MeOH, THF
RT, 15 min
RT, 15 min
LiAlH4
THF
Reflux, 3 h
Reflux, 3 h
NaBH(OAc)3
DCE
-20 °C, 3 h, 65 % (4 steps)
-20 °C, 3 h, 65 % (4 steps)
H2, Pd(OH)2/C
4 atm
MeOH
RT, 2 d, 70 %
4 atm
RT, 2 d, 70 %
+ 
K2CO3
DMF, H2O
0 °C, 12 h, 80 %
0 °C, 12 h, 80 %
3,5-Dimethoxybenzaldehyde, NaBH(OAc)3
DCE, AcOH
0 °C to RT, 12 h, 86 %
0 °C to RT, 12 h, 86 %
Pd(PPh3)4, KOPh
THF
Reflux, 2 h, 56 %
Reflux, 2 h, 56 %
HCl
THF, H2O
55 °C, 10 h
55 °C, 10 h
Malonic Acid, NaOAc
Ac2O, AcOH
120 °C, 2 h, 43 % (2 steps)
120 °C, 2 h, 43 % (2 steps)
