Synthesis of coleon U 12-methyl ether.
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概要
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Reduction of 11-benzoyloxy-12-methoxyabieta-8,11,13-trien-7-one with sodium borohydride, followed by dehydration of the resulting alcohols with <I>p</I>-toluenesulfonic acid, afforded the corresponding 6,8,11,13-tetraene derivative. This was converted into 11-benzoyloxy-12-methoxyabieta-8,11,13-trien-6-one (<B>8</B>) <I>via</I> an epoxide. The 6-oxo compound (<B>8</B>) was reduced with lithium aluminium hydride. Subsequent oxidation of the resulting alcohol with <I>m</I>-chloroperbenzoic acid afforded 6β-hydroxy-12-methoxyabieta-8,12-diene-11,14-dione. This compound was further transformed into 11,14-diacetoxy-12-methoxyabieta-8,11,13-trien-6-one (<B>13</B>) by a series of reactions: Jones oxidation, reduction with a mixture of zinc powder and hydrochloric acid, and acetylation. The diacetate (<B>13</B>) was then oxidized with Jones reagent and the 6,7-dioxo product was immediately converted into 11-acetoxy-6,14-dihydroxy-12-methoxyabieta-5,8,11,13-tetraene (<B>15</B>) by repeated column chromatography on silica gel. The tetraene (<B>15</B>) was finally hydrolyzed with hydrobromic acid to give coleon U 12-methyl ether.
- 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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Takeda Shoji
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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