38 Fraginの構造と合成

概要

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Fragin (I), C_<13>H_<27>O_3N_3, was isolated by the present autho s from cultured broth of a soil bacterium belonging to Pseudomonas fragi as an inhibitor of the growth of chlorella, fungi and some higher plants. The presence in (I) of an unique N-nitrosohydroxylamino group was deduced from the acidity, colour reactions and spectral data. The formation of caprylic acid on acid hydrolysis together with the IR and NMR spectra of (I) suggested the presence of a secondary caprylamide group in this compound. The NMR spectrum of (IV) clarified the function of the remaining five carbon atoms to be -NHCH_2COCH(CH_3)_2. Further, the series of reactions shown in Fig. 3 established the structure of Fragin as (I). Then, (±)-Fragin was synthesized by the route summarized in Fig. 6. The IR spectrum (in CCl_4) and NMR spectrum (in CDCl_3) of the synthetic Fragin were completely identical with those of natural one. As expected, the synthesized sample showed almost about a half antifungal activity of the natural compound against Asp. niger.
天然有機化合物討論会の論文
1967-09-25