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Synthesis of Wasabidienones B1 and B0
L. Pouységu, M. Marguerit, J. Gagnepain, G. Lyvinec, A. J. Eatherton, S. Quideau*
Université de Bordeaux, Institut Européen de Chimie et Biologie, Pessac, France and GlaxoSmithKline, Harlow, UK
25 May 2009 (online)
Wasabidienones B0 and B1 were isolated from Phoma wasabiae Yokogi, a fungus causing widespread destruction of rape, cabbage and wasabi. The o-quinol framework is rather unusual in nature, since most of these compounds readily undergo Diels-Alder dimerization. The focal step of this synthesis is an oxidative dearomatization of the phenol F using SIBX, a commercial, stabilized, non-explosive form of IBX as the oxidant.