Cyclobutane-Containing Scaffolds as Useful Intermediates in the Stereoselective Synthesis of Suitable Candidates for Biomedical Purposes

Efficient and versatile synthetic methodologies are reported for the preparation of products that are suitable candidates to be used as surfactants, gelators for hydroxylic solvents or metal cation ligands, with potential use in several fields including biomedical applications. The common structural...

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Detalles Bibliográficos
Autores: Illa, Ona|||0000-0001-7390-4893, Serra, Albert, Ardiaca, Agustí, Herrero, Xavier, Closa, Guillem|||0000-0002-1333-171X, Ortuño Mingarro, Rosa María|||0000-0001-7635-7354
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:213152
Acceso en línea:https://ddd.uab.cat/record/213152
https://dx.doi.org/urn:doi:10.3390/ijms20184333
Access Level:acceso abierto
Palabra clave:Cyclobutane
Amphiphiles
Surfactants
Gelators
Cation ligands
Descripción
Sumario:Efficient and versatile synthetic methodologies are reported for the preparation of products that are suitable candidates to be used as surfactants, gelators for hydroxylic solvents or metal cation ligands, with potential use in several fields including biomedical applications. The common structural feature of all the synthesized products is the presence of a cis or trans-1,2- or cis-1,3-difunctionalized cyclobutane ring. In the two first cases, the key intermediates including enantiomerically pure 1,3-diamines and 1,3-amino alcohols have been prepared from β-amino acid derivatives obtained, in turn, from a chiral half-ester. This compound is also precursor of γ-amino esters. Furthermore, two kind of polydentate ligands have also been synthesized from a symmetric 1,5-diamine obtained from norpinic acid, which was easily prepared from commercial verbenone.