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Buchler GmbH
D-38110 Braunschweig
Harxb
Ütteler Strasse 3
Tel.  ++ 49  5307  93121
eMail: himstedt@buchler-gmbh.com
and   
 wedde@buchler-gmbh.com

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quinine   quinic acid
Per  year  several hundred tons  of Cinchona alkaloids are extracted
from the bark of the Cinchona ledgeriana. Of all known alkaloids they
are
the mostly used compounds for commercial purposes.

cinchonine

   cinchonalinks.gif (2141 Byte)
R = OMe    Quinine
R = H         Cinchonidine

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Quinine and other Cinchona alkaloids are extracted from the bark of the Cinchona tree, which is mainly cultivated in Afrika, Latin-Amerika and Indonesia

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R = OMe    Quinidine
R = H         Cinchonine

cinchonine

Cinchona Alkaloids

Enantioselective Catalysts

                         .
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-
portant 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 and
sharpless dihydroxylation.



One aspect of their application as ligand
accelerated catalyst  (LAC)
is their
bidentate nature which allows
optimal binding to transition
metals.

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E.J. Corey, J. Am. Chem. Soc.
1997, 119, 12414
enantioselective enolate alkylation
under phase
transfer conditions



enantioselectiveunten.gif (2736 Byte)
[(DHQD)2-PHAL]

K. Barry Sharpless, J. Am Chem. Soc.
1994,
116, 1278
enatioselective osmium-catalyzed
asymmetric dihydroxylation

chinchione  cinchonidine

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quinine
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