IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B
Autor/es:
SIMONETTI, S. O.; LARGHI, E. L.; BRACCA A. B. J.; KAUFMAN, T. S.
Revista:
ORGANIC & BIOMOLECULAR CHEMISTRY
Editorial:
ROYAL SOC CHEMISTRY
Referencias:
Lugar: CAMBRIDGE; Año: 2012 vol. 10 p. 4124 - 4134
ISSN:
1477-0520
Resumen:
The synthesis of the tricyclic angular chromone structure originally assigned to aspergillitine is reported. The synthesis was achieved in 11 steps and 15% overall yield from 2,4-dihydroxypropiophenone, through the intermediacy of 2,3-dimethyl-7-hydroxychromen-4-one. Construction of the nitrogen-bearing heterocyclic ring entailed a Stille cross-coupling reaction with n-Bu3SnCH2CHCH2, followed by double bond isomerization, oximation of the chromone carbonyl, and a final microwave-assisted electrocyclization of the thus formed 6π-electron aza-triene system.
