The synthesis of ar-abietatrien-12,16-oxide and its C-15 epimer.
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概要
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In order to elucidate the absolute configuration of C-15 in natural ar-abietatrien-12,16-oxide, (15<I>R</I>)-12,16-epoxy-8,11,13-abietatriene (<B>1a</B>) and its (15<I>S</I>)-epimer (<B>1b</B>) have been synthesized. Treatment of (15<I>R</I>)-8,11,13-abietatriene-12,16-diol with a mixture of chloromethyl methyl ether, dicyclohexano-18-crown-6, and potassium carbonate afforded <B>1a</B> as a minor product and (15<I>R</I>)-12-methoxymethyl ether as a major product. The latter was further converted into <B>1a</B>. A similar treatment of (15<I>S</I>)-8,11,13-abietatriene-12,16-diol gave <B>1b</B>. Catalytic hydrogenations of 12,16-epoxy-8,11,13,15-abietatetraene, methyl 12,16-epoxy-8,11,13,15-abietatetraen-19-oate (<B>5</B>), and methyl 12,16-epoxy-8,11,13,15-abietatetraen-18-oate (<B>7</B>) afforded the corresponding (15<I>R</I>)-dihydrobenzofuran derivatives and their (15<I>S</I>)-epimers. Conversions of the hydrogenation products from <B>5</B> and <B>7</B> into <B>1a</B> and <B>1b</B> were also carried out. The synthetic <B>1a</B> was identical with natural ar-abietatrien-12,16-oxide.
- 公益社団法人 日本化学会の論文
著者
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Yoshinari Takashi
Department Of Biological And Environmental Chemistry Faculty Of Agriculture Tottori 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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Tsuruta Kazuaki
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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