Syntheses of (3S, 4R, 15S)-4,15-Dimethyl-1,5-dioxa-3-(3′-formamidosalicylamido)-cyclopentadecane-2,6-dione and Its (15R)-Epimer, New Antimycin Analogs
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概要
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A new type of antimycin analogs, (3S, 4R, 15S)-4,15-dimethyl-l,5-dioxa-3-(3′-formamidosalicylamido)-cyclopentadecane-2,6-dione (<B>10a</B>) and its (15R)-epimer (<B>10b</B>) have been synthesized. The epimeric fifteenmembered amino-dilactone moieties in <B>10a</B> and <B>10b</B> were synthesized from a masked L-threonine and <I>t</I>-butyl DL-10-hydroxyundecanoate. Each of the separated epimeric amino-dilactones was <I>N</I>-acylated with <I>O</I>-benzyl-3-nitrosalicylic acid <I>N</I>-hydroxysuccinimide ester. Hydrogenation followed by <I>N</I>-formylation afforded the anti-fungal substances,<B>10a</B> and <B>10b</B>. The 10-<I>C</I>-configurations of <B>10a</B> and <B>10b</B> were determined as "S" and "R", respectively. The (15S)-epimer (<B>10a</B>) showed apparently stronger antifungal activity against <I>Piricularia oryzae</I> than that of the (15R)-epimer (<B>10b</B>).
- 公益社団法人 日本化学会の論文
著者
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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
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Umezawa Sumio
Department of Applied Chemistry Engineering Faculty Keio University
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Ishii Keitaro
Department of Applied Chemistry, Faculty of Engineering, Keio University
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