Lebrasseur Nathalie, Gagnepain Julien, Ozanne-Beaudenon Aurélie, Léger Jean-Michel, Quideau Stéphane
Université de Bordeaux, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France.
J Org Chem. 2007 Aug 3;72(16):6280-3. doi: 10.1021/jo0708893. Epub 2007 Jul 12.
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.
SIBX是λ5-碘代烷2-碘氧基苯甲酸（IBX）的非爆炸性制剂，能安全有效地将各种2-烷基苯酚和萘酚羟基化脱芳构化为邻醌或其[4+2]环二聚体。反应通常在室温下进行，使用SIBX在四氢呋喃中形成的悬浮液。在这些条件下，天然产物如萜品酚的环二聚体，以及首次从其各自的酚类前体一步制备出的莽草酸衍生的（±）-grandifloracin。
