Antibiotics of the ostreogrycin complex. Part II. Structure of ostreogrycin A

TLDR: In this article, the structure of ostreogrycin A, an antibiotic produced by the soil organism Streptomyces Ostreogriseus, has been suggested, which yields 4,6-dimethyl-γ-heptanolactone, DL-alanine, proline, and 10-amino-7-methyl-δ-dec-2-enolactone.

Abstract: Structure (XXIII) is suggested for ostreogrycin A, an antibiotic produced by the soil organism Streptomyces ostreogriseus. Acid hydrolysis of “perhydro A,” prepared by complete hydrogenation of the antibiotic, yields inter alia 4,6-dimethyl-γ-heptanolactone, DL-alanine, proline, and 10-amino-7-methyl-δ-dec-2-enolactone. Ozonolysis of the antibiotic with oxidative working-up yields glycine and β-alanine, while reductive ozonolysis yields methyl glyoxal and 2,4-dimethylpent-2-enal. The production of small quantities of glycine and serine on hydrolysis of ostreogrycin A and its reduction products is explained by the presence of an oxazole ring system in the antibiotic.