Stereoselective syntheses of the antihistaminic drug olopatadine and its E-isomer

Practical stereoselective synthetic routes to the antihistaminic drug olopatadine and its E-isomer have been developed, the key steps being a trans stereoselective Wittig olefination using a nonstabilized phosphorus ylide and a stereoselective Heck cyclization. The stereoselectivity of the Wittig re...

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Detalhes bibliográficos
Autores: Bosch Cartes, Joan, Bachs, Jordi, Gómez, Antonia M., Griera Farres, Rosa, Écija, Marta, Amat Tusón, Mercedes
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2012
País:España
Recursos:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/107829
Acesso em linha:https://hdl.handle.net/2445/107829
Access Level:acceso abierto
Palavra-chave:Antihistamínics
Estructura molecular
Síntesi orgànica
Antihistamines
Molecular structure
Organic synthesis
Descrição
Resumo:Practical stereoselective synthetic routes to the antihistaminic drug olopatadine and its E-isomer have been developed, the key steps being a trans stereoselective Wittig olefination using a nonstabilized phosphorus ylide and a stereoselective Heck cyclization. The stereoselectivity of the Wittig reaction depends on both the phosphonium salt anion and the cation present in the base used to generate the ylide.