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

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 sus...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-08, Vol.72 (16), p.6280-6283
Main Authors: Lebrasseur, Nathalie, Gagnepain, Julien, Ozanne-Beaudenon, Aurélie, Léger, Jean-Michel, Quideau, Stéphane
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Chemistry, Organic - methods
Chromatography - methods
Dimerization
Diterpenes - chemistry
Exact sciences and technology
Hydroquinones - chemistry
Hydroxylation
Iodobenzenes
Iodobenzoates - chemistry
Models, Chemical
Molecular Structure
Naphthols - chemistry
Organic chemistry
Phenols - chemistry
Preparations and properties
Stereoisomerism
Terpenoids
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0708893