Synthesis of Strychnine

C21H22N2O2
Principal investigator | K. Peter C. Vollhardt |
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Publication year | 2000 |
Synthesis type | Formal |
Number of steps | 13 (linear) |
References |
Part 1 of 1
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Na2CO3,
MeO(CH2)2OCH2Cl
DMF
RT, 50 min, 86%


HCl
H2O, THF
RT, 3 d

(COCl)2
RT, 14 h, 83% (2 steps)



C2H2,
CpCo(C2H4)2
THF
0 °C, 45 min, 46%

KOH
H2O, MeOH
Reflux, 6 h, 93%

Fe(NO3)3.9H2O
H2O, MeCN, THF
0 °C, 15 min, 77%


Li2CO3
DMA
40 °C, 24 h, 74%

NaOi-Pr
i-PrOH
RT, 16 h, 90%

n-Bu3SnH,
AIBN
PhH
RT, 60 min, 37%
"Also isolated was the Z-isomer (34 % yield)."

HCl
H2O, THF
RT, 3 h, 99%

Remaining...
28% (1 step)
"The yield was 72 % brsm. See : J. Org. Chem. 1993, 58, 7490."
