Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigator	Yuichi Kobayashi
Publication year	2004
Synthesis type	Total
Number of steps	24 (linear)
References	Tetrahedron Lett. 2004, 45, 3783.

Part 1 of 1

intermediate structure

Dimethyl malonate, KOt-Bu, Pd(PPh3)4

THF

50 °C, 3 h

See the Tsuji-Trost Reaction

intermediate structure

KI

DMF

125 °C, 70% (2 steps)

See the Krapcho Decarboxylation

intermediate structure

LiAlH4

intermediate structure

Imidazole, TBDPSCl

63% (2 steps)

intermediate structure

VinylOEt, Hg(OAc)2

190 °C

See the Claisen Rearrangement

intermediate structure

NaBH4

intermediate structure

Et3N, t-BuCOCl

CH2Cl2

66% (3 steps)

intermediate structure

NaBH4, O3

n-PrOH

-78 °C, 81%

intermediate structure

Ph3P, Imidazole, I2

88%

See the Appel Reaction

intermediate structure

BnNH2

Dioxane

100 °C, 98%

intermediate structure

ClCO2Et

PhMe

99%

intermediate structure

NaOEt

EtOH

Reflux

intermediate structure

o-NO2PhSeCN , n-Bu3P
H2O2 , H2O

THF

77% (2 steps)

See the Grieco Dehydration

intermediate structure

MeLi

0 °C

intermediate structure

BzCl

61% (2 steps)

intermediate structure

n-Bu4N+ F-

THF

intermediate structure

HCrO3Cl.Pyr

CH2Cl2

80% (2 steps)

intermediate structure

+

intermediate structure

NaH

THF

RT, 82%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

AD-mix B

0 °C to RT, 89%

See the Sharpless Asymmetric Dihydroxylation

intermediate structure

MeC(OMe)3, Pyr.TsOH

CH2Cl2

intermediate structure

TMSCl

intermediate structure

intermediate structure

K2CO3

MeOH

96% (3 steps)

intermediate structure

i-Bu2AlH

PhMe

intermediate structure

DMF

160 °C, 66% (2 steps)

intermediate structure

Report an error in this part