Chemistry of maduramicin. II. Decarboxylation, abnormal ketalization and dehydration.

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McGahren WJ, Morton GO, Siegel MM, Borders DB, James JC, Ellestad GA

Chemistry of maduramicin. II. Decarboxylation, abnormal ketalization and dehydration.

J Antibiot (Tokyo). 1986 Nov;39(11):1541-50.

PubMed ID
3793623 [ View in PubMed
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Abstract

The behavior of the free acid and ammonium salt of maduramicin towards heat and alcohols is examined. In refluxing lower alcohols the free acid material is decarboxylated. In addition a bisketal decarboxylated compound as well as an A-ring monoketal decarboxylated derivative are formed. Heating the ammonium salt of the ionophores in suspension in water, or dissolved in inert solvents such as heptane or xylene can cause decarboxylation as well as concomitant dehydration of the F-ring. Reaction of dansyl chloride with the free acid of maduramicin can cause dehydration of the B-ring under very mild conditions.

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