Stoffwechselprodukte von Mikroorganismen 221. Mitteilung. (3S, 8E)‐1,3‐Dihydroxy‐8‐decen‐5‐on, ein Stoffwechselprodukt von Streptomyces fimbriatus (MILLARD und BURR 1926)

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Abstract
(3S, 8E)‐1,3‐Dihydroxy‐8‐decen‐5‐one, a Metabolite of Streptomyces fimbriatus (MILLARD and BURR 1926)From the cultures of Streptomyces fimbriatus, strain Tü 2335, the title compound 1 was isolated by solvent extraction, chromatography, and distillation. Its constitution was determined by spectroscopic investigations of 1 and some of its derivatives, and the chirality by transformation to (R)‐1,3‐isopropylidenedioxy‐decane (12); a reference sample of the latter was prepared from (R)‐methyl 3‐hydroxydecanoate (10). In the equilibrium mixture the keto form 1 predominates the two hemiacetals 2a and 2b. Compound 1 is inactive against bacteria, yeasts and fungi.