Synthesis of Streptolidine (Roseonine, Geamine)
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概要
- 論文の詳細を見る
Streptolidine (roseonine, geamine) (<B>1</B>), a guanidino amino acid component of the streptothricin group antibiotics, was synthesized starting from D-ribose (<B>8</B>). The epimino compound (<B>11b</B>) was prepared from <B>8</B> in five synthetic steps. Azidolysis of <B>11b</B> gave the arabino-type compound (<B>12b</B>), which in turn was converted to the key intermediate tribenzyloxycarbamido lactone (<B>23b</B>) by oxidation of <I>C</I>-1. The lactone <B>23b</B> was rearranged to the free lactam (<B>4</B>) after deprotection, and then guanidinated with cyanogen bromide. The identity of the hydrolysis product of this guanidino lactam with natural streptolidine in all respects certified the proposed structure involving the steric configurations.
- 公益社団法人 日本化学会の論文
著者
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Kusumoto Shoichi
Department Of Chemistry Faculty Of Science Osaka University
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Shiba Tetsuo
Department Of Chemistry Faculty Of Science Osaka University
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Tsuji Shinichi
Department of Chemistry, Faculty of Science, Osaka University
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