title: Open analogues of arcyriaflavin A. Synthesis through Diels-Alder reaction between maleimides and 1-aryl-3-tert-butyldimethylsiloxy-1, 3-butadienes.
abstract: The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1, 3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.
authors.affiliation: Laboratorio de Química Orgánica y Farmacéutica, Universidad de Salamanca, Facultad de Farmacia, Campus Miguel de Unamuno, E-37007 Salamanca, Spain.
authors.forename: M
authors.initials: M
authors.lastname: Adeva
authors.forename: H
authors.initials: H
authors.lastname: Sahagún
authors.forename: E
authors.initials: E
authors.lastname: Caballero
authors.forename: R
authors.initials: R
authors.lastname: Peláez-Lamamié De Clairac
authors.forename: M
authors.initials: M
authors.lastname: Medarde
authors.forename: F
authors.initials: F
authors.lastname: Tomé
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001547:Benzaldehydes / Q000737:chemistry; D002070:Butadienes / Q000138:chemical synthesis*; D002227:Carbazoles / Q000138:chemical synthesis*; D006834:Hydrazines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008301:Maleimides / Q000737:chemistry*; D008968:Molecular Conformation; D013302:Streptomyces / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D001547:Benzaldehydes; D002070:Butadienes; D002227:Carbazoles; D006834:Hydrazines; D008301:Maleimides; C089657:arcyriaflavin A