A stereoselective synthesis of (R)-(-)-rolipram from L-glutamic acid

Autores
Díaz Martínez, AdolfoAutor Universidad de Alcalá; Siro Herrero, Jorge G.; García Navío, José LuisAutor Universidad de Alcalá; Vaquero López, Juan J.; Álvarez-Builla Gómez, JulioAutor Universidad de Alcalá
Identificadores
Enlace permanente (URI): http://hdl.handle.net/10017/3591
DOI: 10.1002/chin.199741254
ISSN: 0039-7881
Editor
Verlag
Fecha de publicación
1997
Filiación
Universidad de Alcalá. Departamento de Química Orgánica
Patrocinadores
We gratefully acknowledge ZAMBON GROUP for studentships (to A. D. and J. S.) and financial support.
Cita bibliográfica
Synthesis, 1997, n. 5, p. 559-562
Palabras clave
Glutamic acid
Rolipram
Article
Central nervous system disease
Chemical modification
Chirality
Drug synthesis
Enantiomer
Reaction analysis
Stereochemistry
Tipo de documento
info:eu-repo/semantics/article
Versión
info:eu-repo/semantics/publishedVersion
Versión del editor
http://dx.doi.org/10.1002/chin.199741254
Derechos
(c) Wiley, 1997
Derechos de acceso
info:eu-repo/semantics/openAccess
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Resumen
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.
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