Total synthesis of minosaminomycin.
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概要
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A component of the antibiotic minosaminomycin (<B>1</B>), (−)-1D-1-amino-1-deoxy-<I>myo</I>-inositol (<B>4</B>) was synthesized from D-inositol (<B>3</B>) by catalytic oxidation of an axial hydroxyl group followed by reduction of the ketoxime. Minobiosamine, 1D-1-amino-1-deoxy-4-<I>O</I>-(α-D-kasugaminyl)-<I>myo</I>-inositol (<B>2</B>), was synthesized from 2′,4′-di-<I>N</I>-acetylkasuganobiosamine (<B>9</B>) by a similar method, and separated from the two isomers of <B>2</B>. The total synthesis of <B>1</B> was accomplished by coupling 2′,4′-di-<I>N</I>-benzyloxycarbonylminobiosamine (<B>14</B>) and <I>N</I><SUP>α</SUP>-[(<I>S</I>)-1-benzyloxycarbonyl-3-methylbutylcarbamoyl]enduracididine (<B>15</B>) followed by removal of the protective groups. Compound <B>14</B> was derived from 1,2′,4′-tri-<I>N</I>-benzyloxycarbonylminobiosamine through the formation of the <I>cis</I>-1,2-carbamate. A diastereomer of <B>1</B> was also synthesized using alloenduracididine.
- 公益社団法人 日本化学会の論文
著者
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KONDO Shinichi
Institute of Microbial chemistry
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Maeda Kenji
Institute Of Microbial Chemistry
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Umezawa Hamao
Institute of Bioorganic Chemistry
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Iinuma Katsuharu
Institute of Microbial Chemistry
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