Journal
TETRAHEDRON LETTERS
Volume 53, Issue 47, Pages 6443-6445Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.09.061
Keywords
Acremolin; Antiaromatic heterocycles; N-2,3-Ethenoguanines; NMR spectroscopy; Structural corrigendum
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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 N-2,3-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. (C) 2012 Elsevier Ltd. All rights reserved.
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