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Efficient access to orthoquinols and their [4 + 2] cyclodimers via SIBX-mediated hydroxylative phenol dearomatization
Nathalie Lebrasseur1, Julien Gagnepain, Aurélie Ozanne-Beaudenon
1Université de Bordeaux, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France.
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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