IQUIR   05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Electrocyclization-Mediated Approach to 2-Methyltriclisine, an Unnatural Analog of the Azafluoranthene Alkaloid Triclisine
Autor/es:
SILVEIRA, C. C.; LARGHI, E. L.; MENDES, S. R.; BRACCA, A. B. J.; RINALDI, F.; KAUFMAN, T. S.
Revista:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Editorial:
Wiley-VCH
Referencias:
Año: 2009 vol. 2009 p. 4637 - 4645
ISSN:
1434-193X
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-3,4-dimethoxybenzaldehyde, through the intermediacy of 3,4-dimethoxyfluoren-9-one. Construction of the heterocyclic ring entailed the para-Claisen rearrangement of an allyl-4-fluorenyl ether, followed by isomerization of the resulting 2-allylfluoren-9-one and a microwave-assisted electrocyclization of the aza 6ð-electron system formed by oximation of its carbonyl function.