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Synfacts 2009(6): 0588-0588  
DOI: 10.1055/s-0029-1216681
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Wasabidienones B1 and B0

Contributor(s): Philip Kocienski, Arndt W. Schmidt
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
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Publikationsdatum:
25. Mai 2009 (online)

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Significance

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.