Chemistry of Leucomycins. VIII. Absolute Configuration of Leucomycin and Isoleucomycin

概要

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Structural relationship between demycarosyl-leucomycin-A_3 proposed through X-ray crystallography by Hiramatsu, et al. and leucomycin-A_3 was examined, and it was found that the hydroxyl group at the C-9 position on lactone of the latter underwent allylic rearrangement being transferred to the C-13 position in the former on mild hydrolysis of the latter with dilute hydrochloric acid. On the other hand, isoleucomycin-A_3,whose hydroxyl group at the C-13 position was transferred from C-9 in leucomycin-A_3 without liberation of mycarose portion, was obtained by warm acid treatment of leucomycin-A_3. Configuration on the C-9 position was determined by applying the benzoate or Mills' rule to leucomycin-A_3 and, from the present and previously reported results, the absolute structure of leucomycin-A_3 was elucidated.
公益社団法人日本薬学会の論文
1970-08-25