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Named reactions

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Strychnine

Chemical structure of Strychnine
C21H22N2O2
Author Christopher D. Vanderwal
Publication year 2011
Synthesis type Formal synthesis
Number of steps 9 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
AllylNH2
RT, 44 h, 100%
Chemical structure + Chemical structure
EtOH
RT to 80 °C, 3.5 h, 81%

See the Zincke Reaction
The yield was 100 % brsm.
Chemical structure
KOt-Bu
Sealed tube
THF
80 °C, 3.5 h, 64%

See the Diels-Alder Reaction
Chemical structure

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Part 2 of 3
Chemical structure
Me2SiH(OEt), [Cp*Ru(MeCN)3]PF6
Acetone
0 °C to RT, 2.5 h
Chemical structure
MsCl, Et3N, LiBr
THF
-25 °C to RT, 5 h

See the Finkelstein Reaction
Chemical structure
MeMgBr
Et2O
-78 °C, 35 min, 47% (3 steps)
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Reagent structure
Pd(PPh3)4, i-Pr2NEt
CHCl3, MeCN
0 °C, 3.5 h, 69%
Chemical structure
TMS2NNa, CuBr.Me2S
NMP
0 to 65 °C, 95 min, 10%

See the Brook Rearrangement
See the Michael Addition
Chemical structure

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Remaining...
70% (1 step)

See: Chem. Ind. 1953, 245.
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