Structure of surgumycin, a carbonyl-conjugated pentaenic antibiotic

Degradation products of surgumycin, a pentaenic antibiotic, were investigated. Oxidation of perhydroantibiotic resulted in formation of brassilic acid. Ozonolysis of the antibiotic was followed by either complete reduction of the ozonolysis products and identification of the resultant hydrocarbon or oxidation by the glycol system and identification of the resultant polyols. The structure of the products of the antibiotic successive reduction was also studied. On the basis of the studies, the structure of 28-hydro-23-dehydroxy-24,29-dihydroxyflavofungin was assigned to surgumycin.