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Named reactions

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Strychnine

"Dedicated with affection and respect to Professor Michael P. Cava, whose original work with Woodward provided the inspiration for this project."

Chemical structure of Strychnine
C21H22N2O2
Author Viresh H. Rawal
Publication year 1994
Synthesis type Formal synthesis
Number of steps 15 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
Br(CH2)2Br, NaOH, n-Bu4N+ Br-
MeCN, H2O
RT
Chemical structure
i-Bu2AlH
PhMe
-78 °C, 96% (2 steps)
Chemical structure
BnNH2, MgSO4
Et2O
RT
Chemical structure
TMSCl, NaI
DMF
60 °C, 96% (2 steps)
Chemical structure
ClCO2Me
Acetone
RT
Chemical structure
HCO2NH4, Pd/C
MeOH
RT, 86% (2 steps)
Chemical structure

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Part 2 of 3
Chemical structure
Methyl acrylate, Bu3SnCl, NaBH4
EtOH
70%
Chemical structure
H2Cr2O7.2Pyr, Celite ®
CH2Cl2
RT, 89%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
ClCO2Me, PhNEt2
RT, 85%
Chemical structure
Sealed tube
PhH
185-200 °C, 4 h, 99%

See the Diels-Alder Reaction
Chemical structure
TMSI
CHCl3, MeOH
Reflux, 11 h, 91%
Chemical structure + Chemical structure
K2CO3
Acetone, DMF
82%
Chemical structure
Pd(OAc)2, K2CO3, n-Bu4N+ Cl-
DMF
70 °C, 3 h, 74%

See the Heck Coupling
Chemical structure
HCl
THF, H2O
96%
Chemical structure

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Remaining...
28% (1 step)

The yield was 72 % brsm. See : J. Org. Chem. 1993, 58, 7490.
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