In 1820, it was first isolated and purified from quina bark powder and proved to be an effective drug for treating malaria. In addition to its medicinal value, quinine is also an important chiral catalyst in the field of organic synthesis and is widely used in the field of asymmetric catalysis of small organic molecules.
TBAF (1M solution of THF, 37 L, 0.037 mmol) was added to a solution of 21c (8 mg, 0.028 mmol) in THF (1 mL) at 0 C. The solution was allowed to warm to ambient temperature. concentrated after 12 h. (1S,2S,5S)-2-(hydroxymethyl)-5-vinylquinuclidine ring (21b, 5.1 mg, 78%) was obtained by preparative TLC (CH2Cl2 / MeOH 2:1) as an anhydrous oil.
