Enantiodivergent Synthesis of (R)- and (S)-Rolipram
by
Joachim Demnitz, Luigi LaVecchia, Edmond Bacher, Thomas H. Keller, Thomas Müller, Friedrich Schürch, Hans-Peter Weber and *
Preclinical Research, Novartis Pharma Ltd, CH-4002 Basel, Switzerland
*
Author to whom correspondence should be addressed.
Molecules 1998, 3(3), 107-119; https://doi.org/10.3390/30300107
Received: 2 November 1997 / Accepted: 23 February 1998 / Published: 10 March 1998
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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MDPI and ACS Style
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. https://doi.org/10.3390/30300107
AMA Style
Demnitz J, LaVecchia L, Bacher E, Keller TH, Müller T, Schürch F, Weber H-P, Pombo-Villar E. Enantiodivergent Synthesis of (R)- and (S)-Rolipram. Molecules. 1998; 3(3):107-119. https://doi.org/10.3390/30300107
Chicago/Turabian StyleDemnitz, Joachim; LaVecchia, Luigi; Bacher, Edmond; Keller, Thomas H.; Müller, Thomas; Schürch, Friedrich; Weber, Hans-Peter; Pombo-Villar, Esteban. 1998. "Enantiodivergent Synthesis of (R)- and (S)-Rolipram" Molecules 3, no. 3: 107-119. https://doi.org/10.3390/30300107
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