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Molecules 1998, 3(3), 107-119; doi:10.3390/30300107
Article

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

, , , , , ,  and
Preclinical Research, Novartis Pharma Ltd, CH-4002 Basel, Switzerland
* Author to whom correspondence should be addressed.
Received: 2 November 1997 / Accepted: 23 February 1998 / Published: 10 March 1998
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Abstract

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.
Keywords: Rolipram; phosphodiesterase; circular dichroism (CD) spectra; enantiodivergent synthesis Rolipram; phosphodiesterase; circular dichroism (CD) spectra; enantiodivergent synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Demnitz, J.; LaVecchia, L.; Bacher, E.; Keller, T.H.; Müller, T.; Schürch, F.; Weber, H.-P.; Pombo-Villar, E. Enantiodivergent Synthesis of (R)- and (S)-Rolipram. Molecules 1998, 3, 107-119.

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