1418129-51-7Relevant articles and documents
Synthetic approach for constructing the 1-oxygenated carbazole core and its application to the preparation of natural alkaloids
Bautista, Rafael,Jerezano, Alberto V.,Tamariz, Joaquin
, p. 3327 - 3336,10 (2012/12/11)
An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.