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Named reactions

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Search synthesis

Strychnine

Chemical structure of Strychnine
C21H22N2O2
Author Philip Magnus
Publication year 1992
Synthesis type Total synthesis
Number of steps 28 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
ClCO2CH2CCl3
CH2Cl2
RT, 40 h, 79%

The starting material was made according to: Can. J. Chem. 1964, 42, 489. Also isolated was the unsaturated ester (10 % yield, see next step).
Chemical structure
NaOMe
MeOH
RT, 30 min, 98%
Chemical structure
ClCO2Me, NaOH, Et3NBn+ Cl-
CH2Cl2, H2O
0 °C, 5 h, 86%

See the Schotten-Baumann Reaction
Chemical structure
Zn
AcOH, THF
RT, 10 h, 82%
Chemical structure
PhSCH2CO2H, BOP-Cl, Et3N
CH2Cl2
0 °C, 95 min, 71%
Chemical structure
mCPBA, NaHCO3
CH2Cl2
0 °C, 30 min, 95%
Chemical structure
NaH
THF
0 °C, 105 min, 98%

See the Michael Addition
Chemical structure
(CF3CO)2O, 2,6-Di-tert-butyl-4-methylpyridine
CH2Cl2
RT, 3 h

See the Pummerer Rearrangement
Chemical structure
HgO, CaCO3
THF, H2O
RT, 12 h
Chemical structure
Br(CH2)2OH, DBU
PhMe
RT, 60 min, 81% (3 steps)
Chemical structure
BH3.THF
THF
RT, 60 min, 100%
Chemical structure
NaHCO3
MeOH
Reflux, 16 h
Chemical structure
Hg(OAc)2
AcOH
RT, 60 h, 43% (2 steps)
Chemical structure
Zn, H2SO4
MeOH
Reflux, 30 min, 88%
Chemical structure
NaOMe
MeOH
Reflux, 2 h, 100%
Chemical structure
4-Methoxybenzenesulfonyl chloride, i-Pr2NEt, DMAP
CH2Cl2
0 °C to RT, 24 h, 81%
Chemical structure
LiBH4
THF
50 °C, 19 h, 67%
Chemical structure
HClO4
RT, 24 h, 55%

This product can be obtained from the degradation of natural strychnine and serves as an enantiopure relay.
Chemical structure
TIPSOTf, DBU
CH2Cl2
0 °C to RT, 30 min, 69%
Chemical structure
(EtO)2P(O)CH2CN, TMS2NK
THF
RT, 42 h, 43%

See the Horner-Wadsworth-Emmons Reaction
Also isolated was the Z-isomer (29 % yield) which could be photoisomerized to the desired E-isomer.
Chemical structure
i-Bu2AlH
CH2Cl2
RT, 20 min
Chemical structure
NaBH4
MeOH
RT, 30 min, 31% (2 steps)
Chemical structure
HCl
MeOH, H2O
RT, 15 h, 81%
Chemical structure
TBSOTf, DBU
CH2Cl2
-20 °C, 60%
Chemical structure
Pyr.SO3, Et3N
DMSO
RT, 4 h, 70%

See the Parikh-Doering Oxidation
Chemical structure
Pyr.HF
Pyr
0 °C, 2 h, 60%
Chemical structure
Na.Anthracene
DME
-30 °C to RT, 13.5 h, 90%
Chemical structure
Malonic Acid, NaOAc
Ac2O
Reflux, 2 h, 70%
Chemical structure

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