Acremolin, a stable natural product with an antiaromatic 1H-Azirine (cas 157-17-5) moiety? A structural reorientation

Add time:09/28/2019    Source:infona.pl

Recently, acremolin (4), a novel modified base, was isolated from a marine-derived fungus and claimed to possess a structure with a 1H-Azirine (cas 157-17-5) 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.

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