Synthesis of 3-mono- and 3,5-difunctionalized noriceanes (tetracyclo(5.3.1.02,6.04,9)undecanes) via oxymetallation of 3,5-dehydronoriceane (pentacyclo(5.3.1.02,6.03,5.04,9)undecane). Oxidation of bicyclo(2.1.0)pentane system by mercury(II), thallium(III),

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概要

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• Oxymercuration of 3,5-dehydronoriceane (<B>1</B>) followed by sodium borohydride reduction gives exclusively <I>endo</I>-3-noriceanol in 80% yield. The <I>trans</I>-1,3-addition organomercury intermediate is isolated as <I>endo</I>-3-acetoxy-<I>exo</I>-5-(chloromercurio)noriceane. Oxidation of <B>1</B> with thallium(III) acetate gives three diacetates, <I>exo</I>,<I>exo</I>- and <I>endo</I>,<I>exo</I>-3,5-diacetoxynoriceanes [(<B>9</B>) and (<B>10</B>)] and <I>endo</I>,<I>exo</I>-4,5-diacetoxytetracyclo[5.3.1.0<SUP>2,6</SUP>.0<SUP>3,9</SUP>]undecane (<B>11</B>) in a ratio of 6:61:27 in 68% combined yield. The analogous oxidation of <B>1</B> with lead(IV) acetate gives <B>9</B>, <B>10</B>, and <B>11</B> in a ratio of 50:25:25 in 80% combined yield. On the basis of the stereochemistry of the products as well as the products distribution, we propose that 1,3-bridged metal ion intervenes and plays an important role in the oxymetallation reaction of bicyclo[2.1.0]pentane system.

• 公益社団法人 日本化学会の論文

著者

• Katsushima Takeo

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

• Yamaguchi Ryohei

  Department of Applied Chemistry, Faculty of Engineering, Yokohama National University

• Kawanisi Mituyosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Iemura Satoshi

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

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