Efficient Access to Orthoquinols and Their [4 + 2] Cyclodimers via SIBX-Mediated Hydroxylative Phenol Dearomatization
The Journal of Organic Chemistry2007Vol. 72(16), pp. 6280–6283
Citations Over TimeTop 10% of 2007 papers
Nathalie Lebrasseur, Julien Gagnepain, Aurélie Ozanne‐Beaudenon, Jean‐Michel Léger, Stéphane Quideau
Abstract
SIBX, the nonexplosive formulation of the lambda5-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.
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