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.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:20131 |
| Date | January 2012 |
| Creators | Banert, Klaus |
| Publisher | Technische Universität Chemnitz |
| Source Sets | Hochschulschriftenserver (HSSS) der SLUB Dresden |
| Language | English |
| Detected Language | English |
| Type | doc-type:article, info:eu-repo/semantics/article, doc-type:Text |
| Source | Tetrahedron letters. - 53. 2012, 47, S. 6443 - 6445 |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 10.1016/j.tetlet.2012.09.061, 0040-4039 |
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