276681-04-0Relevant articles and documents
Open analogues of arcyriaflavin A. Synthesis through Diels-Alder reaction between maleimides and 1-aryl-3-tert-butyldimethylsiloxy-1,3- butadienes
Adeva, Marta,Sahagun, Heidi,Caballero, Esther,Pelaez-Lamamie De Clairac, Rafael,Medarde, Manuel,Tome, Fernando
, p. 3387 - 3394 (2000)
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.