A convenient synthesis of (.+-.)-taxodione, (.+-.)-ferruginol, and (.+-.)-sugiol.

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概要

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• The condensation of β-cyclocitral (<B>4</B>); with 3-isopropyl-4-methoxybenzyl chloride (<B>5</B>) in the presence of lithium naphthalenide gave an alcohol (<B>6</B>), which was then oxidized to the corresponding α,β-unsaturated ketone (<B>7</B>). The Intramolecular cyclization of <B>7</B> with polyphosphoric acid yielded (±)-12-methoxyabieta-8,11,13-trien-6-one (<B>8</B>) and its <I>cis</I>-isomer (<B>9</B>), which was then successfully converted into <B>8</B> <I>via</I> an enol acetate (<B>11</B>). The <B>8</B> ketone was dem ethylated with boron tribromide to give a phenol (<B>18</B>), and this was then reduced with lithium aluminium hydride to yield the corresponding alcohol (<B>19</B>). The oxidation of the C-11 position in <B>19</B> with benzoyl peroxide gave (±)-12-benzoyloxyabieta-8,11,13-trien-6β,11-diol (<B>20</B>), which, on reduction with lithium aluminium hydride and subsequent oxidation with Jones reagent, afforded (±)-taxodione (<B>1</B>). The reductive cleavage of the hydroxyl group in <B>6</B> with dichloroaluminium hydride, followed by cyclization, gave (±)-ferruginyl methyl ether (<B>12</B>), which was then demethylated with boron tribromide to produce (±)-ferruginol (<B>2</B>). Further, the oxidation of <B>12</B> with chromium trioxide, followed by demethylation, gave (±)-sugiol (<B>3</B>).

• 公益社団法人 日本化学会の論文

著者

• Usui Shuji

  Department Of Chemistry Faculty Of Science Hiroshima University

• Matsumoto Takashi

  Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima

• Morimoto Toshitaka

  Department of Chemistry, Faculty of Science, Hiroshima University

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