12 Leucomycinの構造

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The structure of a new antibiotic leucomycin A_3 (I) which have been isolated from Streptomyces kitasatoensis Hata are proposed. In the course of chemical degradative and spectroscopic studies on these compounds, interrelations with magnamycins and spiramycins are attempted. I is hydrolyzed in methanol to give VIII and IX, the former is confirmed by analyses of IR, NMR and mass spectra, and the later is treated by concentrated hydrochloric acid to yield XIII which is confirmed with an authentic sample. On the other hand, I is hydrolyzed in a diluted hydrochloric acid to give XV and XVI, the former is methylated to VIII and the later oxygenated to β-hydroxy butylic acid. When I is hydrolyzed after treated with methyl iodide, followed oxidation with sodium periodate to give acetaldehyde in a good yield. From these results, isovaleryl mycarose state to the position 4' of mycaminose, and have the partial structure >C=CH-CH_2-CH.CH_3-O- in I. Hydrogenation of I to yield IV, oxidation of I by an activated manganese dioxide to give VI show the α,β,γ,δ conjugated double bonds and hydroxyl group state in this system. I has an aldehyde from IR and NMR spectra, and from the fact that the data of NMR and UV spectra of III suggested a primary aldehyde, which state on a lactone ring neighboring to mycamino-side, because XXI yielding from XX by oxidation and closed to make a γ-lactone from IR spectrum. Stereochemistry of I are elucidated by IR spectral studies of intramolecular hydrogen bonding and NMR studies of I and related compounds.
天然有機化合物討論会の論文
1966-09-15

12 Leucomycinの構造

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