Journal
ORGANIC LETTERS
Volume 10, Issue 22, Pages 5211-5214Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802183p
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- Institut Universitaire de France (IUF)
- Ministere de la Recherche
- CNRS
- Association Nationale de la Recherche Technique
- GSK
- CIFRE [457/2005]
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The first total synthesis of the natural nondimerizing o-quinol (+)-wasabidienone B-1 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 B-1 was then converted into its congener (-)-wasabidienone B-0 via an improved thermally induced ring-contracting isomerization reaction.
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