Open analogues of arcyriaflavin A. Synthesis through Diels-Alder reaction between maleimides and 1-aryl-3-tert-butyldimethylsiloxy-1, 3-butadienes.
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.
Adeva
M
M
Laboratorio de Química Orgánica y Farmacéutica, Universidad de Salamanca, Facultad de Farmacia, Campus Miguel de Unamuno, E-37007 Salamanca, Spain.
Sahagún
H
H
Caballero
E
E
Peláez-Lamamié De Clairac
R
R
Medarde
M
M
Tomé
F
F
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
D000970:Antineoplastic Agents; D001547:Benzaldehydes; D002070:Butadienes; D002227:Carbazoles; D006834:Hydrazines; D008301:Maleimides; C089657:arcyriaflavin A