Synthesis of Strychnine

C21H22N2O2
Principal investigator | Martin E. Kuehne |
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Publication year | 1998 |
Synthesis type | Total |
Number of steps | 21 (linear) |
References |
Part 1 of 1
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NaBH4,
MgSO4,
PhCHO
MeOH
0 °C to RT, 6 h

Et3N,
Boc2O
CH2Cl2
RT, ON, 89% (2 steps)




Et3N,
TMSOTf
CH2Cl2
0 °C to RT, 60 min, 97%



NH3
MeOH
0 °C to RT, 5 d, 87%
"The yield was 95 % brsm."

i-Pr2NEt,
(CF3CO)2O
CH2Cl2
0 °C to RT, 40 min

KBH4
EtOH
75 °C, 4 h, 76% (2 steps)



n-BuLi
THF
-78 °C, 4.5 h, 73%


TsOH
H2O, THF
RT, 2 h, 82%

DMAP,
Et3N,
Ts2O
DCE, MeOH
0 to 60 °C, 2 h

H2,
PdCl2
1 atm
MeOH
RT, 3 h, 91% (2 steps)


BF3.OEt2,
i-Bu2AlH
CH2Cl2
-78 °C, 3.5 h, 91%

NaBH3CN
AcOH
10 °C, 30 min

NaOMe
MeOH
RT, 2 h, 92% (2 steps)

i-Bu2AlH
CH2Cl2
-90 °C, 30 min, 71%

