Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigator	Martin E. Kuehne
Publication year	1998
Synthesis type	Total
Number of steps	21 (linear)
References	J. Org. Chem. 1998, 63, 9427.

Part 1 of 1

intermediate structure

NaBH4, MgSO4, PhCHO

MeOH

0 °C to RT, 6 h

intermediate structure

Et3N, Boc2O

CH2Cl2

RT, ON, 89% (2 steps)

intermediate structure

+

intermediate structure

Et3N, ZnCl2, t-BuOCl

THF

-78 °C to RT, ON

See the Mannich Reaction

intermediate structure

LiCl

DMF

135 °C, 4 h, 88% (2 steps)

See the Krapcho Decarboxylation

intermediate structure

Et3N, TMSOTf

CH2Cl2

0 °C to RT, 60 min, 97%

intermediate structure

+

intermediate structure

BzOH, Hydroquinone

Dean-Stark

PhH

Reflux, 10 h, 84%

See the Pictet-Spengler Reaction

intermediate structure

NH3

MeOH

0 °C to RT, 5 d, 87%

"The yield was 95 % brsm."

intermediate structure

i-Pr2NEt, (CF3CO)2O

CH2Cl2

0 °C to RT, 40 min

intermediate structure

KBH4

EtOH

75 °C, 4 h, 76% (2 steps)

intermediate structure

KIO4, K2OsO2(OH)4

H2O, THF

0 °C, 4 h, 62%

See the Lemieux-Johnson Oxidation

intermediate structure

+

intermediate structure

n-BuLi

THF

-78 °C, 4.5 h, 73%

intermediate structure

Me2S, Et3N, NCS

PhMe

-20 °C to RT, 80 min, 94%

See the Corey-Kim Oxidation

intermediate structure

TsOH

H2O, THF

RT, 2 h, 82%

intermediate structure

DMAP, Et3N, Ts2O

DCE, MeOH

0 to 60 °C, 2 h

intermediate structure

H2, PdCl2

1 atm

MeOH

RT, 3 h, 91% (2 steps)

intermediate structure

TMS2NK, (EtO)2P(O)CH2CO2Me

THF

0 °C to RT, 8.5 h, 64%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

BF3.OEt2, i-Bu2AlH

CH2Cl2

-78 °C, 3.5 h, 91%

intermediate structure

NaBH3CN

AcOH

10 °C, 30 min

intermediate structure

NaOMe

MeOH

RT, 2 h, 92% (2 steps)

intermediate structure

i-Bu2AlH

CH2Cl2

-90 °C, 30 min, 71%

intermediate structure

Malonic Acid, NaOAc

Ac2O, AcOH

110 °C, 65%

See the Aldol Addition

intermediate structure

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