scholarly journals Optical inversion of (2R)- to (2S)-isomers of 2-(4-(2-oxocyclopentylmethyl)-phenyl)propionic acid (loxoprofen), a new anti-inflammatory agent, and its monohydroxy metabolites in the rat.

1984 ◽  
Vol 32 (1) ◽  
pp. 251-257 ◽  
Author(s):  
HISOMU NAGASHIMA ◽  
YORIHISA TANAKA ◽  
HIDETOSHI WATANABE ◽  
RYOZO HAYASHI ◽  
KATSURO KAWADA
1973 ◽  
Vol 4 (48) ◽  
pp. no-no
Author(s):  
R. W. J. CARNEY ◽  
J. J. CHART ◽  
R. GOLDSTEIN ◽  
N. HOWIE ◽  
J. WOJTKUNSKI

1973 ◽  
Vol 29 (8) ◽  
pp. 938-938 ◽  
Author(s):  
R. W. J. Carney ◽  
J. J. Chart ◽  
R. Goldstein ◽  
Nancy Howie ◽  
Janice Wojtkunski

1983 ◽  
Vol 33 ◽  
pp. 122
Author(s):  
Takeshi Yamaguchi ◽  
Takayoshi Kojima ◽  
Yoshio Iizuka ◽  
Masaaki Sasaki ◽  
Kazu Kobayashi ◽  
...  

2000 ◽  
Vol 55 (5) ◽  
pp. 369-372 ◽  
Author(s):  
Henri Brunner ◽  
Peter Schmidt

2-Aryl-substituted propionic acids, such as the important anti-inflammatory agent Naproxen, exist in two enantiomeric forms. The (S)-enantiomer of 2-(6-methoxynaphth-2-yl)propionic acid 1 is about 28 times more effective than the (S)-enantiomer. A new catalytic method to synthesize Naproxen (S)-1 involves the enantioselective decarboxylation of suitably substituted malonic acid derivatives. Thus, 2-(6-methoxynaphth-2-yl)-2-methylmalonic acid 6 and its monoester 7 were stirred in THF with catalytic amounts of chiral bases, which induced decarboxylation. After work-up, optical inductions up to 39.8% ee were found in the resulting products 1 and 9. The optically active bases may be fully recycled by extraction.


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