info:eu-repo/semantics/article
Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B
Fecha
2012-03Registro en:
Simonetti, Sebastián Osvaldo; Larghi, Enrique Leandro; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul; Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 10; 3-2012; 4124-4134
1477-0520
1477-0539
CONICET Digital
CONICET
Autor
Simonetti, Sebastián Osvaldo
Larghi, Enrique Leandro
Bracca, Andrea Beatriz Juana
Kaufman, Teodoro Saul
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.