Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization.

Laurent Pouységu, Mélanie Marguerit, Julien Gagnepain, Gildas Lyvinec, Andrew J Eatherton, Stéphane Quideau

Institut des Sciences Moléculaires, CNRS-UMR 5255, Université de Bordeaux, Pessac Cedex, France.

Organic letters 2008 Nov 20

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The first total synthesis of the natural nondimerizing o-quinol (+)-wasabidienone B1 was achieved from commercially available 1,3,5-trimethoxybenzene. The key dearomatizing transformation was efficiently accomplished via a hydroxylative phenol dearomatization reaction using the stabilized lambda(5)-iodane reagent IBX (SIBX). (+)-Wasabidienone B1 was then converted into its congener (-)-wasabidienone B0 via an improved thermally induced ring-contracting isomerization reaction.

Citation

Laurent Pouységu, Mélanie Marguerit, Julien Gagnepain, Gildas Lyvinec, Andrew J Eatherton, Stéphane Quideau. Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization. Organic letters. 2008 Nov 20;10(22):5211-4