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Lebrasseur, Nathalie; Gagnepain, Julien; Ozanne-Beaudenon, Aurélie; Léger, Jean-Michel; Quideau, Stéphane
Journal of organic chemistry, 08/2007, Letnik: 72, Številka: 16Journal Article
SIBX, the nonexplosive formulation of the λ5-iodane 2-iodoxybenzioc acid (IBX), safely and efficiently mediates the hydroxylative dearomatization of various 2-alkylphenols and napthols into orthoquinols or their 4 + 2 cyclodimers. Reactions are typically run at room temperature using SIBX as a suspension in THF. Using these conditions, natural products such as the cyclodimer of the terpene carvacrol and, for the first time, the shikimate-derived (±)-grandifloracin were prepared in one step from their respective phenolic precursor.
