Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization |
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Authors: | Pouységu Laurent Marguerit Mélanie Gagnepain Julien Lyvinec Gildas Eatherton Andrew J Quideau Stéphane |
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Affiliation: | Institut des Sciences Moléculaires, CNRS-UMR 5255, Université de Bordeaux, Pessac Cedex, France. |
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Abstract: | 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. |
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