A hypervalent iodine-mediated spirocyclization of 2-(4-hydroxybenzamido)acrylates--unexpected formation of δ-spirolactones.

نویسندگان

  • Christian Hempel
  • Nicole M Weckenmann
  • C Maichle-Moessmer
  • Boris J Nachtsheim
چکیده

On the way towards a new total synthesis of (S)-arogenate, a novel aryl-λ(3)-iodane-mediated oxidative spirocyclization of para-substituted phenol derivatives has been discovered. Starting from easy accessible 2-(4-hydroxybenzamido)acrylates we could construct spirocyclic lactams in up to 52% yield. Under alternative reaction conditions the same precursors underwent an unexpected oxidative spirocyclization yielding a novel δ-spirolactone in up to 70% yield.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 10 47  شماره 

صفحات  -

تاریخ انتشار 2012