Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigator	Eric N. Jacobsen
Publication year	2004
Synthesis type	Total
Number of steps	18 (linear)
References	J. Am. Chem. Soc. 2004, 126, 706.

Part 1 of 1

intermediate structure

+

intermediate structure

n-BuLi

THF

-78 to 0 °C, 2 h, 84%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

Special reagent

Methyl Cyanoacetate

Cyclohexane, t-BuOH

RT, 48 h, 91%

See the Michael Addition

intermediate structure

H2, Ni (Raney)

43 atm

MeOH

80 °C, 14 h, 89%

intermediate structure

H2O, i-Pr2NLi

THF

-78 °C to RT, 50 min

intermediate structure

LiAlH4

THF

0 to 35 °C, 11 h

intermediate structure

(BnOCO)2O, Et3N

CH2Cl2

0 °C to RT, 4 h, 51% (3 steps)

"Also isolated was the C3-epimer (19 % yield)."

intermediate structure

NMO, n-Pr4N+ RuO4-

4 Å MS

CH2Cl2

RT, 60 min

See the Ley-Griffith Oxidation

intermediate structure

Ph3P+CH3 Br-, KOt-Bu

THF

0 °C to RT, 13 h, 73% (2 steps)

See the Wittig Reaction

intermediate structure

n-Bu4N+ F-

THF

0 °C, 4 h

intermediate structure

n-Pr4N+ RuO4-, NMO

4 Å MS

CH2Cl2

RT, 60 min, 86% 2 steps)

See the Ley-Griffith Oxidation

intermediate structure

+

intermediate structure

CrCl2

THF

RT, 12 h, 79%

See the Takai Reaction

intermediate structure

+

intermediate structure

Special reagent

K3PO4, Pd(OAc)2

THF

RT, 16 h, 89%

See the Suzuki Coupling

intermediate structure

AD-mix B, MsNH2

t-BuOH

0 °C, 12 h, 88%

See the Sharpless Asymmetric Dihydroxylation

intermediate structure

MeC(OMe)3, Pyr.TsOH

CH2Cl2

RT, 12 h

intermediate structure

AcBr

CH2Cl2

0 °C to RT, 6 h

intermediate structure

intermediate structure

K2CO3

MeOH

RT, 2 h, 81% (3 steps)

intermediate structure

Et2AlCl, PhSMe

CH2Cl2

0 °C to RT, 8 h

intermediate structure

µW

MeCN

185 °C, 20 min, 68% (2 steps)

intermediate structure

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