Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorViresh H. Rawal
Publication year1994
Synthesis typeFormal
Number of steps 15 (3 parts)
References
J. Org. Chem. 1994, 59, 2685. J. Am. Chem. Soc. 1993, 115, 3030.
Part 1 of 3
intermediate structure
NaOH, Br(CH2)2Br, n-Bu4N+ Br-
H2O, MeCN
RT
intermediate structure
i-Bu2AlH
PhMe
-78 °C, 96% (2 steps)
intermediate structure
MgSO4, BnNH2
Et2O
RT
intermediate structure
NaI, TMSCl
DMF
60 °C, 96% (2 steps)
intermediate structure
ClCO2Me
Acetone
RT
intermediate structure
Pd/C, HCO2NH4
MeOH
RT, 86% (2 steps)
intermediate structure
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Part 2 of 3
intermediate structure
NaBH4, n-Bu3SnCl, Methyl acrylate
hν
EtOH
70%
intermediate structure
H2Cr2O7.2Pyr, Celite
CH2Cl2
RT, 89%
intermediate structure
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Part 3 of 3
intermediate structure + intermediate structure
ClCO2Me, PhNEt2
RT, 85%
intermediate structure
Sealed tube
PhH
185-200 °C, 4 h, 99%
See the Diels-Alder Reaction
intermediate structure
TMSI
CHCl3, MeOH
Reflux, 11 h, 91%
intermediate structure + intermediate structure
K2CO3
Acetone, DMF
82%
intermediate structure
K2CO3, Pd(OAc)2, n-Bu4N+ Cl-
DMF
70 °C, 3 h, 74%
See the Mizoroki-Heck Reaction
intermediate structure
HCl
H2O, THF
96%
intermediate structure
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Remaining...
28% (1 step)
"The yield was 72 % brsm. See : J. Org. Chem. 1993, 58, 7490."
intermediate structure