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Org Lett. 2008 Nov 20;10(22):5211-4. doi: 10.1021/ol802183p. Epub 2008 Oct 22.

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

Author information

1
Institut des Sciences Moléculaires, CNRS-UMR 5255, Université de Bordeaux, Pessac Cedex, France.

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.

PMID:
18939801
DOI:
10.1021/ol802183p
[Indexed for MEDLINE]

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