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

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Authors
Díaz Martínez, AdolfoUniversity of Alcalá Author; Siro Herrero, Jorge G.; García Navío, José LuisUniversity of Alcalá Author; Vaquero López, Juan JoséUniversity of Alcalá Author; Álvarez-Builla Gómez, JulioUniversity of Alcalá Author
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/3591
DOI: 10.1002/chin.199741254
ISSN: 0039-7881
Publisher
Verlag
Date
1997
Academic Departments
Universidad de Alcalá. Departamento de Química Orgánica
Teaching unit
Unidad docente Química Orgánica
Funders
We gratefully acknowledge ZAMBON GROUP for studentships (to A. D. and J. S.) and financial support.
Bibliographic citation
Synthesis, 1997, n. 5, p. 559-562
Keywords
Glutamic acid
Rolipram
Article
Central nervous system disease
Chemical modification
Chirality
Drug synthesis
Enantiomer
Reaction analysis
Stereochemistry
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Publisher's version
http://dx.doi.org/10.1002/chin.199741254
Rights
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Access rights
info:eu-repo/semantics/openAccess
Abstract
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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