Synthesis of Strychnine

Structure of Strychnine

C21H22N2O2

Principal investigator	David W. C. MacMillan
Publication year	2011
Synthesis type	Total
Number of steps	12 (linear)
References	Nature 2011, 475, 183.

Part 1 of 1

intermediate structure

NaH, (4-MeOPh)CH2Cl

DMF

0 °C to RT, 35 min, 94%

intermediate structure

SeO2

Dioxane , H2O

100 °C, 5 h, 87%

intermediate structure

TMS2NK, 18-Crown-6, (EtO)2P(O)CH2SeMe

THF

-78 °C to RT, 90 min, 81%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

+

intermediate structure

Special reagent

Br3CCO2H

PhMe

-60 °C to RT, 23 h, 82%

See the Michael Addition

intermediate structure

(Ph3P)3RhCl

PhMe, PhCN

120 °C, 5.5 h, 86%

intermediate structure

MeOH, Phosgene, Et3N

PhMe

-45 °C to RT, 3 h, 88%

intermediate structure

CF3CO2H, i-Bu2AlH

CH2Cl2, MeOH

-78 °C to RT, 3 h, 81%

intermediate structure

+

intermediate structure

DBU, K2CO3

DMF

RT, 50 min, 84%

intermediate structure

i-Bu2AlH

CH2Cl2

-78 °C, 2 h, 91%

intermediate structure

NaHCO3, Pd(OAc)2, n-Bu4N+ Cl-

EtOAc

RT, 24 h, 58%

See the Mizoroki-Heck Reaction

intermediate structure

PhSH

CF3CO2H

45 °C, 13 h, 66%

intermediate structure

Malonic Acid, NaOAc

Ac2O, AcOH

120 °C, 2 h, 69%

See the Aldol Addition

intermediate structure

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