IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
congresos y reuniones científicas
Título:
An Approach to the Synthesis of 2-Methyltriclisine, an Un-natural Analog of Triclisine, Employing a Microwave-Assisted Electrocyclization
Autor/es:
SILVEIRA, C. C.; LARGHI, E. L.; MENDES, S. R.; BRACCA, A. B. J.; RINALDI, F.; KAUFMAN, T. K.
Lugar:
San Pedro, Brasil, 31 de Agosto al 4 de Setiembre de 2009
Reunión:
Congreso; 13th Brazilian Meeting on Organic Synthesis; 2009
Institución organizadora:
Comité Organizador 13 BMOS
Resumen:
The synthesis of 2-methyltriclisine, an unnatural analog of the azafluoranthene alkaloid triclisine, is reported. The synthesis was achieved in 10 steps and 21% overall yield from 2-bromo-4-dimethoxybenzaldehyde, through the intermediacy of 3,4-dimethoxyfluoren-9-one. Construction of the heterocyclic ring entailed the para-Claisen rearrangement ofan allyl-4-fluorenyl ether, followed by isomerization of the resulting 2-allylfluoren-9-one and a microwave-assisted electrocyclization of the aza (6-phi)-electron system formed by oximation of its carbonyl function.
