Diels-alder cycloaddition in the synthesis of 1-azafagomine, analogs, and deriv...

• Autor(es): Salgueiro, D. A. L. ; Sousa, Cristina ; Fortes, A. Gil ; Alves, M. José
• Data: 2012
• Identificador Persistente: http://hdl.handle.net/1822/22060
• Origem: RepositóriUM - Universidade do Minho
• Assunto(s): Azafagomine; Biological activity; Diels-alder cycloaddition; Glycosidase inhibitors; Monocyclic analogs; Azasugars
• Tipo de Documento: Artigo
• Idioma: Inglês

Descrição

This comprehensive review deals with the synthesis of 1-azafagomine, analogs, and derivatives having the Diels-Alder cycloaddition as the key step. Most of the compounds referred are racemic or have been resolved by lipase transesterification. There are two asymmetric cycloadditions leading to 1-azafagomine or to an analog. In one case both enantiomers of 1-azafagomine were prepared together with a pair of derivatives. The study comprises glycosidase inhibition studies of the target compounds to a set of glycosidic enzymes, and evidenced molecular features that enhance or diminish their activity as glycosidase inhibitors.