• Media type: E-Article
  • Title: Acremolin, a stable natural product with an antiaromatic 1H-azirine moiety? A structural reorientation
  • Contributor: Banert, Klaus [Author]
  • Published: Chemnitz: Technische Universität Chemnitz, [2014]
  • Language: English
  • DOI: 10.1016/j.tetlet.2012.09.061
  • Keywords: antiaromatic heterocycles ; NMR-Spektroskopie ; NMR spectroscopy ; structural corrigendum ; antiaromatische Heterocyclen ; Strukturberichtigung ; Acremolin
  • Origination:
  • Footnote: Quelle: Tetrahedron letters. - 53. 2012, 47, S. 6443 - 6445
  • Description: Recently, acremolin (4), a novel modified base, was isolated from a marine-derived fungus and claimed to possess a structure with a 1H-azirine moiety. It is shown now that the reported NMR data are not compatible with this antiaromatic heterocycle, which should be an extremely unstable compound. An isomeric, substituted N2,3-ethenoguanine is presented as a plausible alternative structure of acremolin that is consistent with all spectroscopic data. Thus, 1H-azirines keep their classification as very short-lived intermediates.