Abstract
REDUCTION of aspergillic acid, C12H20O2N2, an antibiotic isolated from culture filtrates of Aspergillus flavus1, gives in high yield a neutral reaction product, deoxyaspergillic acid, C12H20ON2, to which the structure 2-hydroxy-3 : 6-disec.-butylpyrazine has been ascribed2. We have previously described syntheses of 2-hydroxy-3 : 6-disec.-butylpyrazine8, and although We were unable to resolve the racemic compound, a comparison of its properties with those of deoxyaspergillic acid led us to conclude that the latter is a hydroxypyrazine derivative. Substantial differences in the intensity of light absorption in the ultra-violet, however, suggested that the two compounds differ more profoundly than in stereochemical orientation. Moreover, deoxyaspergillic acid has been racemized by treatment with alkali, and the racemate is distinct from 2-hydroxy-3 : 6-disec.-butylpyrazine, which is itself unaffected by similar treatment with alkali.
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