Efficient Access to Orthoquinols and Their [4 + 2] Cyclodimers via SIBX-Mediated Hydroxylative Phenol Dearomatization

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• 作者：Nathalie Lebrasseur ; Julien Gagnepain ; Aur&eacute ; lie Ozanne-Beaudenon ; Jean-Michel L&eacute ; ger ; St&eacute ; phane Quideau
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 3, 2007
• 年：2007
• 卷：72
• 期：16
• 页码：6280 - 6283
• 全文大小：103K
• 年卷期：v.72,no.16(August 3, 2007)
• ISSN：1520-6904

文摘

SIBX, the nonexplosive formulation of the ⁵-iodane 2-iodoxybenzioc acid (IBX), safely and efficiently mediates thehydroxylative dearomatization of various 2-alkylphenols andnapthols into orthoquinols or their [4 + 2] cyclodimers.Reactions are typically run at room temperature using SIBXas a suspension in THF. Using these conditions, naturalproducts such as the cyclodimer of the terpene carvacrol and,for the first time, the shikimate-derived (±)-grandifloracinwere prepared in one step from their respective phenolicprecursor.