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
NaH, Pd2(dba)3, Ph3P
THF
RT, , 91%
intermediate structure
NaBH3CN, TiCl4
THF
-78 °C, , 98%
intermediate structure + intermediate structure
CuCl, DCC
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
(Me3Sn)2, LiCl, Pd(PPh3)4
THF
60 °C, , 80%
See the Stille Coupling
intermediate structure + intermediate structure
CO, LiCl, Pd2(dba)3, Ph3As
NMP
70 °C, , 80%
See the Stille Coupling
intermediate structure
t-BuOOH, Me3N+Bn HO-
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
i-Pr2NEt, MsCl
CH2Cl2
-23 °C
intermediate structure
LiCl
RT
intermediate structure
CF3CONH2, NaH
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
H2SO4, Zn
H2O, MeOH
Reflux
intermediate structure
NaOMe
MeOH
RT
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, , 52% (3 steps)
intermediate structure
Ac2O, Malonic Acid, NaOAc
AcOH
110 °C, , 65%
intermediate structure