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Acremolin, a stable natural product with an antiaromatic 1H-azirine moiety? A structural reorientation

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.

Identiferoai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:20131
Date January 2012
CreatorsBanert, Klaus
PublisherTechnische Universität Chemnitz
Source SetsHochschulschriftenserver (HSSS) der SLUB Dresden
LanguageEnglish
Detected LanguageEnglish
Typedoc-type:article, info:eu-repo/semantics/article, doc-type:Text
SourceTetrahedron letters. - 53. 2012, 47, S. 6443 - 6445
Rightsinfo:eu-repo/semantics/openAccess
Relation10.1016/j.tetlet.2012.09.061, 0040-4039

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