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Named reactions

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Search synthesis

Strychnine

Chemical structure of Strychnine
C21H22N2O2
Author Larry E. Overman
Publication year 1993
Synthesis type Total synthesis
Number of steps 24 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
NaH, Pd2(dba)3, Ph3P
THF
RT, 91%

See the Tsuji-Trost Reaction
Chemical structure
NaBH3CN, TiCl4
THF
-78 °C, 98%
Chemical structure
+
Chemical structure
DCC, CuCl
PhH
80 °C, 91%
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C
Chemical structure
TIPSCl, 1,1,3,3-Tetramethylguanidine
NMP
-10 °C, 65% (2 steps)
Chemical structure
CrO3, H2SO4
Acetone, H2O
-5 °C, 97%

See the Jones Oxidation
Chemical structure
  1. Li(s-Bu)3BH
  2. PhNTf2
THF
-78 to 0 °C, 88%
Chemical structure
(Me3Sn)2, Pd(PPh3)4, LiCl
THF
60 °C, 80%

See the Stille Coupling
Chemical structure + Chemical structure
CO, Pd2(dba)3, Ph3As, LiCl
3.5 atm
NMP
70 °C, 80%

See the Stille Coupling
Chemical structure
t-BuOOH, Me3N+Bn HO-
THF
-15 °C, 91%

See the Michael Addition
Chemical structure
Ph3P=CH2
THF
0 °C to RT, 92%

See the Wittig Reaction
Chemical structure
n-Bu4N+ F-
THF
-15 °C, 100%
Chemical structure
MsCl, i-Pr2NEt
CH2Cl2
-23 °C
Chemical structure
LiCl
RT

See the Finkelstein Reaction
Chemical structure
CF3CONH2, NaH
DMF
RT
Chemical structure
NaH
PhH
100 °C
Chemical structure
KOH
EtOH, H2O
60 °C, 43% (5 steps)
Chemical structure
(CH2O)n, Na2SO4
MeCN
80 °C, 98%

See the Cope Rearrangement
Chemical structure
  1. i-Pr2NLi
  2. MeO2CCN
THF
-78 °C

See the Claisen Condensation
Chemical structure
HCl
MeOH
Reflux, 70% (2 steps)
Chemical structure
Zn, H2SO4
MeOH, H2O
Reflux
Chemical structure
NaOMe
MeOH
RT
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 52% (3 steps)
Chemical structure
Malonic Acid, Ac2O, NaOAc
AcOH
110 °C, 65%
Chemical structure

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