Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Chemistry of Leucomycins. VIII. Absolute Configuration of Leucomycin and Isoleucomycin
大村 智中川 彰片桐 通子秦 藤樹平松 幹夫木村 皓俊納谷 恵三
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ジャーナル フリー

1970 年 18 巻 8 号 p. 1501-1508

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Structural relationship between demycarosyl-leucomycin-A3 proposed through X-ray crystallography by Hiramatsu, et al. and leucomycin-A3 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-A3, whose hydroxyl group at the C-13 position was transferred from C-9 in leucomycin-A3 without liberation of mycarose portion, was obtained by warm acid treatment of leucomycin-A3. Configuration on the C-9 position was determined by applying the benzoate or Mills' rule to leucomycin-A3 and, from the present and previously reported results, the absolute structure of leucomycin-A3 was elucidated.
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© The Pharmaceutical Society of Japan
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