INVESTIGADORES
BRACCA Andrea Beatriz Juana
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-V C H VERLAG GMBH
Referencias:
Lugar: Weinheim; 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.
