%0 Journal Article
%T Enantiodivergent Synthesis of (R)- and (S)-Rolipram
%A Joachim Demnitz
%A Luigi LaVecchia
%A Edmond Bacher
%A Thomas H. Keller
%A Thomas M¨¹ller
%A Friedrich Sch¨¹rch
%A Hans-Peter Weber
%A Esteban Pombo-Villar
%J Molecules
%D 1998
%I MDPI AG
%R 10.3390/30300107
%X Both enantiomers of rolipram (1) have been prepared in large quantity from a common intermediate rac-3-(3¡¯-cyclopentyloxy-4¡¯-methoxy)phenyl-4-nitro butyric acid (6), which was resolved by way of the two readily separable diastereoisomeric amides obtained with (S)-(-)-phenylethylamine. Reduction of the nitro group and intramolecular transamidation gave (R)-(-)-1 and (S)-(+)-1, respectively. CD spectra of both enantiomers of rolipram are reported and discussed. Both enantiomers of rolipram presented the same potency of inhibitory activity against recombinant cyclic-AMP-selective phosphodiesterase (PDE4) subtypes.
%K Rolipram
%K phosphodiesterase
%K circular dichroism (CD) spectra
%K enantiodivergent synthesis
%U http://www.mdpi.com/1420-3049/3/3/107