Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigator	Joan Bosch
Publication year	2000
Synthesis type	Total
Number of steps	14 (linear)
References	Chem. Eur. J. 2000, 6, 655. J. Am. Chem. Soc. 1997, 119, 7230.

Part 1 of 1

intermediate structure

O3

CH2Cl2

-78 °C, 3 h

intermediate structure

+

intermediate structure

NaBH3CN

i-PrOH

RT, 2 d, 37% (2 steps)

intermediate structure

ClCO2CH(Cl)CH3

135 °C, 2 d, 72%

intermediate structure

TMS2NH, TMSI

CH2Cl2, Pentane

-20 °C, 6 h, 100%

intermediate structure

(PhSe)2, PhSeCl

THF

-35 °C to RT, 4.5 h, 70%

intermediate structure

O3, i-Pr2NH

CH2Cl2

-78 °C to RT, 72%

intermediate structure

MeOH

Reflux, 3 h, 100%

intermediate structure

+

intermediate structure

LiI, K2CO3

MeCN

50 °C, 3 h, 74%

intermediate structure

Ph3P, Pd(OAc)2

Et3N

90 °C, 90 min, 53%

See the Mizoroki-Heck Reaction

intermediate structure

MeO2CCN, TMS2NLi

HMPA, THF

-78 °C to RT, 4.5 h, 62%

"The yield was 67 % brsm."

intermediate structure

H2SO4, Zn

MeOH

Reflux, 2 h, 36%

intermediate structure

NaOMe

MeOH

Reflux, 5 h, 72%

intermediate structure

i-Bu2AlH

PhMe

-40 °C, 25 min

intermediate structure

Malonic Acid, NaOAc

Ac2O, AcOH

110 °C, 2 h, 49% (2 steps)

See the Aldol Addition

intermediate structure

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