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Enantiodivergent Synthesis of (R)- and (S)-Rolipram

Author(s): Joachim Demnitz | Luigi LaVecchia | Edmond Bacher | Thomas H. Keller | Thomas Müller | Friedrich Schürch | Hans-Peter Weber | Esteban Pombo-Villar

Journal: Molecules
ISSN 1420-3049

Volume: 3;
Issue: 3;
Start page: 107;
Date: 1998;
Original page

Keywords: Rolipram | phosphodiesterase | circular dichroism (CD) spectra | enantiodivergent synthesis

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.
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