Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigator	Gilbert Stork
Publication year	2001
Synthesis type	Total
Number of steps	17 (linear)
References	J. Am. Chem. Soc. 2001, 123, 3239.

Part 1 of 1

intermediate structure

AlMe3, Et2NH

CH2Cl2

0 °C to RT, ON, 82%

intermediate structure

Imidazole, TBSCl

CH2Cl2

RT, 18 h, 97%

intermediate structure

+

intermediate structure

i-Pr2NLi

THF

-78 °C to RT, 5 h, 79%

intermediate structure

Pyr.TsOH

EtOH

RT, ON, 93%

intermediate structure

Xylene(s)

Reflux, 12 h, 97%

intermediate structure

i-Bu2AlH

THF

-78 °C, 5 h

intermediate structure

TMS2NK, Ph3P+CH2OMe Cl-

THF

-78 °C to RT, ON, 75% (2 steps)

See the Wittig Reaction

intermediate structure

Ph3P, (PhO)2P(O)N3, DEAD

THF

0 °C, 24 h, 95%

See the Mitsunobu Reaction

intermediate structure

HCl

CH2Cl2, H2O, THF

RT, 8 h, 78%

intermediate structure

+

intermediate structure

i-Pr2NLi

THF

-78 to 0 °C, 65 min, 72%

intermediate structure

(COCl)2, DMSO, Et3N

CH2Cl2

-78 °C to RT, 90 min, 85%

See the Swern Oxidation

intermediate structure

Ph3P

THF

Reflux, 3 h, 81%

See the Wittig Reaction

intermediate structure

NaBH4

MeOH, THF

RT, 3 h, 91%

intermediate structure

HF

H2O, MeCN

RT, 60 min, 95%

intermediate structure

MsCl, Pyr

CH2Cl2

RT, ON

intermediate structure

MeCN

Reflux, 3 h, 68% (2 steps)

intermediate structure

NaH, O2

DMSO

70 °C, 45 min, 78%

intermediate structure

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