RESUMO
A mild, diastereoselective synthesis of fused lactone-pyrrolidinones using an oxidative radical cyclization is reported. The methodology is demonstrated in a formal synthesis of (-)-salinosporamide A.
Assuntos
Lactonas/síntese química , Pirróis/síntese química , Pirrolidinonas/síntese química , Ciclização , Lactonas/química , Estrutura Molecular , Oxirredução , Pirróis/química , Pirrolidinonas/química , EstereoisomerismoRESUMO
A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans ß-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure-function relationships are warranted.
Assuntos
Macrolídeos/síntese química , Biofilmes/efeitos dos fármacos , Macrolídeos/química , Estrutura Molecular , Myxococcales/química , Streptococcus mutans/efeitos dos fármacosRESUMO
Manganese(III) acetate mediated oxidative radical cyclizations have been used to synthesize a range of densely functionalized and sterically congested cyclopentane-lactones. A number of the resulting lactones contain vicinal all-carbon quaternary stereocenters adjacent to a tertiary benzylic stereocenter and are formed with high levels of stereocontrol.