Monday, November 4, 2013

Cinchona Alkaloids from Cinchona Bark

Cinchona alkaloids  are widely  used  in the    pharmaceutical    and   chemical industry.  The  most popular compound Quinine  is   a    valuable   antimalarial agent  and  muscle relaxant  compound for more than 100  years,  its  „pseudo enantiomer“  Quinidine   is  used as  a cardiac   depressant   (antiarrhythmic).
Furthermore   Quinine  is  also  an   im-important bitter agent  in the beverage (soft drink) industry.

Cinchonine    and    Cinchonidine  are widespread   resolving   agents   particu-larly for  acids.  Cinchona  alkaloids  and their modified  derivatives are significant  chiral catalysts in asymmetric syntheses for example Corey enolalkylation & sharp-less dihydroxylation.

One aspect of their application as ligand accelerated catalyst  (LAC) is their bidentate nature which allows optimal binding to transition metals.
 
Per year several hundred tons of Cinchona alkaloids are extracted
from the bark of the Cinchona ledgeriana and Cinchona Succirubra. Of all known alkaloids they are the mostly used compounds for commercial purposes.

cinchonine
   cinchonalinks.gif (2141 Byte)
R = OMe    Quinine
R = H         Cinchonidine
baumrindenernte.jpg (13248 Byte)
Quinine and other Cinchona alkaloids are extracted from the bark of the Cinchona tree, which is mainly cultivated in Afrika, Latin-Amerika and Indonesia
cinchonarechts.gif (2268 Byte)
R = OMe    Quinidine
R =
  


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