IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Total synthesis and cytotoxic activity of 6,8-dimethoxy-1,3-dimethyl- isoquinoline, isolated from Ancistrocladus tectorius. A 6π-azaelectrocyclization approach
Autor/es:
IVÁN CORTÉS; TEODORO S. KAUFMAN; BORINI ETICHETTI, CARLA M.; ANDREA B. J. BRACCA; JAVIER E. GIRARDINI
Revista:
SYNTHESIS-STUTTGART
Editorial:
GEORG THIEME VERLAG KG
Referencias:
Lugar: Nueva York; Año: 2019 vol. 51 p. 433 - 440
ISSN:
0039-7881
Resumen:
A facile and convenient approach toward the total synthesisof 1,3-dimethyl-6,8-dimethoxyisoquinoline from phloroacetophenoneis reported. The sequence entailed the selective 2,4-di-O-methylationand further triflation of the resulting phenolic product. This was followedby a Stille-type allylation, an allyl-to-propenyl isomerization, andthe methoximation of the carbonyl moiety. A final microwave-assisted6π-azaelectrocyclization completed the sequence. Functionalized derivativeson C-1 were also prepared. The heterocycles exhibited cytotoxicactivity.
