Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorAlbert Padwa
Publication year2007
Synthesis typeTotal
Number of steps 17 (linear)
References
Org. Lett. 2007, 9, 279. J. Org. Chem. 2004, 69, 3735.
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
µW
PhMe
150 °C, 3 h, 95%
See the Diels-Alder Reaction
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
Pd(OH)2/C, H2
4 atm
MeOH
RT, 2 d, 70%
intermediate structure + intermediate structure
K2CO3
DMF, H2O
0 °C, 12 h, 80%
intermediate structure
NaBH(OAc)3, 3,5-Dimethoxybenzaldehyde
AcOH, DCE
0 °C to RT, 12 h, 86%
intermediate structure
NMO, n-Pr4N+ RuO4-
4Å MS
MeCN
0 °C to RT, 2.5 h, 80%
See the Ley-Griffith Oxidation
intermediate structure
Pd(PPh3)4, KOPh
THF
Reflux, 2 h, 56%
intermediate structure
i-Pr2NLi, Ph2P(O)CH2OMe
THF
0 °C to RT, 25 h, 72%
See the Horner-Wadsworth-Emmons Reaction
intermediate structure
HCl
H2O, THF
55 °C, 10 h
intermediate structure
Malonic Acid, NaOAc
Ac2O, AcOH
120 °C, 2 h, 43% (2 steps)
intermediate structure
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