90334-19-3Relevant articles and documents
Efficient access to orthoquinols and their [4 + 2] cyclodimers via SIBX-mediated hydroxylative phenol dearomatization
Lebrasseur, Nathalie,Gagnepain, Julien,Ozanne-Beaudenon, Aurelie,Leger, Jean-Michel,Quideau, Stephane
, p. 6280 - 6283 (2007)
(Chemical Equation Presented) 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.
Regio- and stereoselectivities in Diels-Alder cyclodimerizations of orthoquinonoid cyclohexa-2,4-dienones
Gagnepain, Julien,Méreau, Rapha?l,Dejugnac, Delphine,Léger, Jean-Michel,Castet, Frédéric,Deffieux, Denis,Pouységu, Laurent,Quideau, Stéphane
, p. 6493 - 6505 (2008/02/08)
The [4+2] cyclodimerization of cyclohexa-2,4-dienone derivatives of the orthoquinone monoketal and orthoquinol types has been the topic of numerous investigations over the last 50 years in the aim of rationalizing the extraordinary level of regio-, site-,