Efficient access to orthoquinols and their [4 + 2] cyclodimers via SIBX-mediated hydroxylative phenol dearomatization.
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.
Lebrasseur
Nathalie
N
Université de Bordeaux, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France.
Gagnepain
Julien
J
Ozanne-Beaudenon
Aurélie
A
Léger
Jean-Michel
JM
Quideau
Stéphane
S
D002625:Chemistry, Organic / Q000379:methods*; D002845:Chromatography / Q000379:methods; D019281:Dimerization; D004224:Diterpenes / Q000737:chemistry; D006873:Hydroquinones / Q000737:chemistry*; D006900:Hydroxylation; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
D004224:Diterpenes; D006873:Hydroquinones; D007462:Iodobenzenes; D007463:Iodobenzoates; D009284:Naphthols; D010636:Phenols; C014576:grandiflorenic acid; C476101:o-iodoxybenzoic acid