Synthesis of Strychnine

C21H22N2O2
Principal investigator | Masakatsu Shibasaki |
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Publication year | 2002 |
Synthesis type | Total |
Number of steps | 31 (linear) |
References |
Part 1 of 1
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2-Ethyl-2-methyl-1,3-dioxolane,
TsOH
RT, 16 h




TiCl4,
NaBH3CN
CH2Cl2, THF
-78 to -55 °C, 10.5 h

DCC,
CuCl
PhH
Reflux, 5 h, 70% (2 steps)

i-Bu2AlH
CH2Cl2
-78 °C, 60 min

Et3N,
TIPSOTf
CH2Cl2
-78 °C, 10 min, 98% (2 steps)

Camphorsulfonic acid
Acetone
RT, 2 d, 62%
"The yield was 90 % brsm."

LiTMP,
TMSCl
THF
-78 °C, 2 h


TMSCl,
i-Pr2NLi
THF
-78 °C, 2 h


DBU
CH2Cl2
RT, 60 min, 57% (3 steps)

I2,
DMAP
CH2Cl2
RT, 5 h, 89%



TMS(CH2)2OCH2Cl,
i-Pr2NEt
CH2Cl2
4 °C to RT, 24 h, 100%

Et3N.3HF
THF
RT, 2.5 d, 100%



Zn,
NH4Cl
H2O, MeOH
RT, 2 h, 77% (2 steps)

Me2SSMe+ BF4-
4Å MS
CH2Cl2
RT, 3 h, 86%

NaBH3CN,
TiCl4
CH2Cl2, THF
-78 °C, 65 min, 68%

HCl
H2O, MeOH
55 °C, 3 h

Ac2O
Pyr
RT, 36 h

NaOMe
MeOH
RT, 30 min

TIPSCl,
Imidazole
CH2Cl2, DMF
4 °C, 2 h, 51% (4 steps)

NiCl2,
NaBH4
EtOH, MeOH
RT, 40 min, 33%
"The yield was 94 % brsm."


Et3N.3HF
THF
RT, 12 h, 83% (2 steps)

NaOMe
MeOH
40 °C, 2 d

