Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigatorLarry E. Overman
Publication year1993
Synthesis typeTotal
Number of steps 24 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Ph3P, Pd2(dba)3, NaH
THF
RT, 91%
intermediate structure
TiCl4, NaBH3CN
THF
-78 °C, 98%
intermediate structure + intermediate structure
DCC, CuCl
PhH
80 °C, 91%
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C
intermediate structure
1,1,3,3-Tetramethylguanidine, TIPSCl
NMP
-10 °C, 65% (2 steps)
intermediate structure
CrO3, H2SO4
Acetone, H2O
-5 °C, 97%
See the Jones Oxidation
intermediate structure
  1. Li(s-Bu)3BH
  2. PhNTf2
THF
-78 to 0 °C, 88%
intermediate structure
Pd(PPh3)4, LiCl, (Me3Sn)2
THF
60 °C, 80%
See the Stille Coupling
intermediate structure + intermediate structure
Ph3As, Pd2(dba)3, LiCl, CO
3.5 atm
NMP
70 °C, 80%
See the Stille Coupling
intermediate structure
Me3N+Bn HO-, t-BuOOH
THF
-15 °C, 91%
intermediate structure
Ph3P=CH2
THF
0 °C to RT, 92%
See the Wittig Reaction
intermediate structure
n-Bu4N+ F-
THF
-15 °C, 100%
intermediate structure
MsCl, i-Pr2NEt
CH2Cl2
-23 °C
intermediate structure
LiCl
RT
intermediate structure
NaH, CF3CONH2
DMF
RT
intermediate structure
NaH
PhH
100 °C
intermediate structure
KOH
EtOH, H2O
60 °C, 43% (5 steps)
intermediate structure
(CH2O)n, Na2SO4
MeCN
80 °C, 98%
intermediate structure
  1. i-Pr2NLi
  2. MeO2CCN
THF
-78 °C
intermediate structure
HCl
MeOH
Reflux, 70% (2 steps)
intermediate structure
Zn, H2SO4
H2O, MeOH
Reflux
intermediate structure
NaOMe
MeOH
RT
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 52% (3 steps)
intermediate structure
NaOAc, Malonic Acid, Ac2O
AcOH
110 °C, 65%
intermediate structure