Tetrahedron Asymmetry p. 3257 - 3266 (2001)
Update date:2022-08-05
Topics: Reactivity Lewis Acids Experimental terms Polyhydroxyalkyl-heterocycles
Moreno-Vargas
Fernandez-Bolaos
Fuentes
Robina
We report the reactivity of different polyhydroxyalkyl-heterocycles towards ceric ammonium nitrate (CAN) and ferric chloride. The behaviour of 2-methyl-5-(tetritol-1-yl)-pyrroles and -furans is different towards CAN oxidation. Pyrroles afford 2,5-diformylheterocycles, while furans give access to 1,4-dicarbonyl compounds containing three stereogenic centres. Ferric chloride promotes an intramolecular C-arylation reaction on O-benzylated-polyhydroxyalkyl furans, yielding an isochroman moiety, which is the basic skeleton of a variety of natural products.
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(2021)
