Syntheses of recyclized macrolide antibiotics and related derivatives from mycaminosyltylonolide.
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概要
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Mycaminosyltylonolide diethyl acetal was, after reduction of the 9-keto group, hydrolyzed, and the seco-acids obtained were recyclized to give new 16-membered (9<I>R</I>)- and (9<I>S</I>)-hydroxy macrolide derivatives, in which the 23-hydroxyl group of the starting substance was incorporated into the macrolactone ring. Selective oxidation of the (9<I>S</I>)-hydroxy derivative (<B>15</B>) with DDQ gave the keto compound (<B>18</B>). Removal of the acetal-protecting groups gave a new macrolide (<B>19</B>), which is antibacterial. Several other <I>O</I>-acetyl derivatives were also prepared and their antibacterial activities were measured. By the <SUP>1</SUP>H- and <SUP>13</SUP>C-NMR spectroscopies of 3,23-di-<I>O</I>-acetylmycaminosyltylonolide diethyl acetal by varying the temperature, the presence of two rotamers was clarified.
- 公益社団法人 日本化学会の論文
著者
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Tanaka Akihiro
Institute For Drug Discovery Research Yamanouchi Pharmaceutical Co. Ltd.
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Tsuchiya Tsutomu
Institute of Bioorganic Chemistry
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Umezawa Sumio
Institute of Bioorganic Chemistry
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Watanabe Azuma
Institute of Bioorganic Chemistry
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Kobayashi Reiko
Institute of Bioorganic Chemistry
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