The synthesis of coleon B tri-O-methyl ether.
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概要
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Methyl (+)-12-benzoyloxy-11,14-dioxo-8,12-abietadien-18-oate was converted into methyl 11,12,14-trimethoxy-8,11,13-abietatrien-18-oate (<B>8</B>). The Grignard reaction of <B>8</B> with phenylmagnesium bromide, followed by oxidation with lead tetraacetate, afforded 11,12,14-trimethoxy-19-norabieta-4(18),8,11,13-tetraene. This was then converted into 3α-bromo-11,12,14-trimethoxy-18-norabieta-8,11,13-trien-2-one (<B>15</B>) by a series of reactions: selenium dioxide oxidation, catalytic hydrogenation, dehydration, hydroxybromination, and Jones oxidation. Acetalization of <B>15</B> with 1,2-ethanediol, followed by oxidation with Jones reagent and then with oxygen in the presence of potassium <I>t</I>-butoxide, afforded 3-bromo-2,2-ethylenedioxy-6-hydroxy-11,12,14-tri-methoxy-18-norabieta-5,8,11,13-tetraen-7-one, which was converted into (−)-coleon B tri-<I>O</I>-methyl ether (<B>4</B>) by hydrolysis and dehydrobromination. Another conversion of <B>15</B> into <B>4</B> was also achieved by a series of reactions: debromination, acetalization, Collins oxidation, oxygen oxidation, hydrolysis, and dehydrogenation.
- 公益社団法人 日本化学会の論文
著者
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Goto Fumitaka
Department Of Electrical And Computer Engineering Nagoya Institute Of Technology
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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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Nishizaki Katsumi
Department of Chemistry, Faculty of Science, Hiroshima University
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Kurihara Fumio
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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Goto Fumitaka
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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