Revision of structures of nellionol and dehydronellionol.
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概要
- 論文の詳細を見る
The structures of nellionol and dehydronellionol were revised respectively to 6α,11,12,16-tetrahydroxyabieta-8,11,13-trien-7-one (<B>12</B>) and 6,11,12,16-tetrahydroxyabieta-5,8,11,13-tetraen-7-one (<B>13</B>) by the following syntheses. A mixture of (15<I>R</I>)- and (15<I>S</I>)-12-methoxyabieta-8,11,13-trien-16-ol, prepared from 13-acetyl-12-methoxypodocarpa-8,11,13-triene, was converted into 11,12,16-triacetoxyabieta-8,11,13-trien-7-one (<B>22</B>) <I>via</I> 16-acetoxy-12-benzoyloxyabieta-8,11,13-trien-11-ol. Treatment of <B>22</B> with isopropenyl acetate, followed by oxidation with <I>m</I>-chloroperbenzoic acid and subsequent acetylation, afforded 6α, 11,12,16-tetraacetoxyabieta-8,11,13-trien-7-one, which was hydrolyzed with dilute hydrochloric acid to <B>12</B>. The ketone <B>22</B> was also converted into <B>13</B> <I>via</I> 11,12,16-triacetoxyabieta-8,11,13-trien-6-one. The spectral data of <B>12</B> and <B>13</B> were in good agreement with those of natural nellionol and dehydronellionol.
- 公益社団法人 日本化学会の論文
著者
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Takeda Shoji
Department Of Biomaterials Osaka Dental University
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Matsumoto Takashi
Department Of Applied Physics Waseda University
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Imai Sachihiko
Department of Chemistry, Faculty of Science, Hiroshima University
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Mitsuki Masanori
Department of Chemistry, Faculty of Science, Hiroshima University
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Matsumoto Takashi
Department of Applied Material Science, Faculty of Integrated Arts and Science, University of Tokushima
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