Synthetic approach for constructing the 1-oxygenated carbazole core and its application to the preparation of natural alkaloids
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.
Bautista, Rafael,Jerezano, Alberto V.,Tamariz, Joaquin
p. 3327 - 3336,10
(2012/12/11)
Synthetic approach for constructing the 1-oxygenated carbazole core and its application to the preparation of natural alkaloids
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. Georg Thieme Verlag Stuttgart · New York.
Bautista, Rafael,Jerezano, Alberto V.,Tamariz, Joaquín
p. 3327 - 3336
(2013/01/15)
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