title: Novel degradation products from the treatment of salinomycin and narasin with formic acid.
abstract: 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.
authors.affiliation: Central Research Division, Pfizer Inc., Groton, Connecticut 06340.
authors.forename: J L
authors.initials: JL
authors.lastname: Wells
authors.forename: J
authors.initials: J
authors.lastname: Bordner
authors.forename: P
authors.initials: P
authors.lastname: Bowles
authors.forename: J W
authors.initials: JW
authors.lastname: McFarland
mesh_terms: D003049:Coccidiostats; D005561:Formates; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011714:Pyrans; D013329:Structure-Activity Relationship; D000095662:Polyether Polyketides
chemical_list: D003049:Coccidiostats; D005561:Formates; D011714:Pyrans; C030544:formic acid; C010327:salinomycin; D000095662:Polyether Polyketides; C013612:narasin