Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorK. Peter C. Vollhardt
Publication year2000
Synthesis typeFormal
Number of steps 13 (linear)
References
Org. Lett. 2000, 2, 2479.
Part 1 of 1
intermediate structure
Na2CO3, MeO(CH2)2OCH2Cl
DMF
RT, 50 min, 86%
intermediate structure
Trimethylsilylacetylene, Pd(PPh3)2Cl2, CuI
Et3N
RT, 60 min, 98%
See the Sonogashira Coupling
intermediate structure
HCl
H2O, THF
RT, 3 d
intermediate structure
(COCl)2
RT, 14 h, 83% (2 steps)
intermediate structure + intermediate structure
n-Bu4N+ Cl-, NaOH
CH2Cl2, H2O
0 °C, 50 min, 86%
See the Schotten-Baumann Reaction
intermediate structure
C2H2, CpCo(C2H4)2
THF
0 °C, 45 min, 46%
intermediate structure
KOH
H2O, MeOH
Reflux, 6 h, 93%
intermediate structure
Fe(NO3)3.9H2O
H2O, MeCN, THF
0 °C, 15 min, 77%
intermediate structure + intermediate structure
Li2CO3
DMA
40 °C, 24 h, 74%
intermediate structure
NaOi-Pr
i-PrOH
RT, 16 h, 90%
intermediate structure
n-Bu3SnH, AIBN
PhH
RT, 60 min, 37%
"Also isolated was the Z-isomer (34 % yield)."
intermediate structure
HCl
H2O, THF
RT, 3 h, 99%
intermediate structure
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Remaining...
28% (1 step)
"The yield was 72 % brsm. See : J. Org. Chem. 1993, 58, 7490."
intermediate structure