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Synthesis 1997; 1997(5): 559-562
DOI: 10.1055/s-1997-3182
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A Stereoselective Synthesis of (R)-(-)-rolipram from L-Glutamic Acid

Adolfo Diaz, Jorge G. Siro, José L. García-Navío, Juan J. Vaquero, Julio Alvarez-Builla*
  • *Departamento de Química Orgánica, Universidad de Alcalá, E-28871 Alcalá de Henares, Madrid, Spain, Fax +34(1)8854686; Internet: jalvarez@quimor.alcala.es
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Publication Date:
31 December 2000 (online)

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A stereoselective synthesis of (R)-(-)-rolipram from L-glutamic acid is described. The key step is a stereoselective Michael addition of an arylcuprate to a modified pyroglutamic derivative which acts as the template to induce the stereoselectivity. Facile manipulation of the enantiomerically pure Michael product afforded the expected therapeutic agent.

(R)-(-)-rolipram - L-glutamic acid - Michael addition - regiocontrol

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