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

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


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydroxylation
  • Indicators and Reagents / chemistry
  • Iodobenzenes / chemistry*
  • Isomerism
  • Lactones / chemical synthesis*
  • Phenols / chemistry*
  • Quinones / chemical synthesis*


  • Indicators and Reagents
  • Iodobenzenes
  • Lactones
  • Phenols
  • Quinones
  • wasabidienone B0
  • wasabidienone B1
  • o-iodoxybenzoic acid