Revision of structure of anhydronellionol triacetate.
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概要
- 論文の詳細を見る
The structure of anhydronellionol triacetate was revised to 11,12,16-triacetoxy-6-hydroxyabieta-5,8,11,13-tetraen-7-one (<B>18</B>) by the following syntheses. Acetylation of 16-acetoxyabieta-8,11,13-trien-12-ol, followed by oxidation with chromium trioxide, afforded 12,16-diacetoxyabieta-8,11,13-trien-7-one. This was converted into 6,12,16-triacetoxyabieta-5,8,11,13-tetraen-7-one (<B>17</B>) <I>via</I> 12,16-diacetoxyabieta-8,11,13-trien-6-one. Oxidation of 11,12,16-triacetoxyabieta-8,11,13-trien-6-one with Jones reagent gave <B>18</B>, whose <SUP>1</SUP>H NMR spectrum was in good agreement with that of natural anhydronellionol triacetate. 11,12,16-Triacetoxyabieta-5,8,11,13-tetraen-7-one (<B>28</B>) was also synthesized from 11,12,16-triacetoxyabieta-8,11,13-trien-7-one. The <SUP>1</SUP>H NMR spectra of <B>17</B> and <B>28</B> were different from that of natural anhydronellionol triacetate. Since the revised structure <B>18</B> corresponds to dehydronellionol triacetate, the name of anhydronellionol should now be dropped from the list of natural diterpenes.
- 公益社団法人 日本化学会の論文
著者
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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 Chemistry, Faculty of Science, Hiroshima University
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Matsumoto Takashi
Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima
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Maeta Seiji
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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