Novel degradation products from the treatment of salinomycin and narasin with formic acid

Salinomycin and narasin (4-methylsalinomycin) upon treatment with HCO2H furnish the known furanone fragment 3 and the complementary but rearranged fragments 1 and 2 respectively. The structure of 1 has been established by X-ray analysis. Upon being heated under reflux in PhMe, 1 undergoes the retrog...

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Veröffentlicht in:	Journal of medicinal chemistry 1988-01, Vol.31 (1), p.274-276
Hauptverfasser:	Wells, Jennie L, Bordner, Jon, Bowles, Paul, McFarland, James W
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Coccidiostats Exact sciences and technology Formates Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Magnetic Resonance Spectroscopy Mass Spectrometry Organic chemistry Preparations and properties Pyrans Structure-Activity Relationship
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Zusammenfassung:	Salinomycin and narasin (4-methylsalinomycin) upon treatment with HCO2H furnish the known furanone fragment 3 and the complementary but rearranged fragments 1 and 2 respectively. The structure of 1 has been established by X-ray analysis. Upon being heated under reflux in PhMe, 1 undergoes the retrograde aldol reaction to furnish alpha, gamma-dimethyl-2-furanbutanal (4). The furan moiety of 1 is more resistant to electrophilic substitution than expected, but it can be acylated by highly reactive reagents such as (CF3CO)2O and AcOSO2Me. Compounds 1 and 2, the acetyl and trifluoracetyl derivatives of the former, and the reduction products thereof have no significant anticoccidial activity.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00396a045