Synthesis of Strychnine

C21H22N2O2
Principal investigator | Larry E. Overman |
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Publication year | 1993 |
Synthesis type | Total |
Number of steps | 24 (linear) |
References |
Part 1 of 1
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TiCl4,
NaBH3CN
THF
-78 °C, 98%


DCC,
CuCl
PhH
80 °C, 91%

i-Bu2AlH
CH2Cl2
-78 °C

1,1,3,3-Tetramethylguanidine,
TIPSCl
NMP
-10 °C, 65% (2 steps)


- Li(s-Bu)3BH
- PhNTf2
THF
-78 to 0 °C, 88%






n-Bu4N+ F-
THF
-15 °C, 100%

MsCl,
i-Pr2NEt
CH2Cl2
-23 °C


NaH,
CF3CONH2
DMF
RT

NaH
PhH
100 °C

KOH
EtOH, H2O
60 °C, 43% (5 steps)



HCl
MeOH
Reflux, 70% (2 steps)

Zn,
H2SO4
H2O, MeOH
Reflux

NaOMe
MeOH
RT

i-Bu2AlH
CH2Cl2
-78 °C, 52% (3 steps)

NaOAc,
Malonic Acid,
Ac2O
AcOH
110 °C, 65%
