The total synthesis of (+)-taxoquinone, (-)-7.ALPHA.-acetoxyroyleanone, (-)-dehydroroyleanone, (-)-horminone, (-)-7-oxoroyleanone, and (+)-inuroyleanol.
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概要
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Methylation of 12-benzoyloxyabieta-8,11,13-trien-11-ol with methyl iodide afforded 11-benzoyloxy-12-methoxyabieta- and 12-benzoyloxy-11-methoxyabieta-8,11,13-triene (<B>9</B>). Oxidation of the latter product with chromium trioxide, followed by sodium borohydride reduction and acetylation, gave 7β-acetoxy-12-benzoyloxy-11-methoxyabieta-8,11,13-triene (<B>17</B>) and its 7α-acetoxy isomer (<B>18</B>) in a ratio of <I>ca.</I> 5 : 1. On the other hand, treatment of <B>9</B> with lead tetraacetate produced <B>17</B> and <B>18</B> in a ratio oi <I>ca.</I> 1 : 2. The 7β-acetate (<B>17</B>) was then oxidized with chromium trioxide and the resulting <I>p</I>-quinone derivative was hydrolyzed with aqueous sodium hydroxide to give taxoquinone (<B>1</B>), which on dehydration gave dehydroroyleanone. Similarly, the 7α-acetate (<B>18</B>) was converted into horminone (<B>4</B>) <I>via</I> the <I>p</I>-quinone derivative, which was treated with aqueous sodium hydrogencarbonate to give 7α-acetoxyroyleanone. Oxidation of <B>4</B> with manganese dioxide afforded 7-oxoroyleanone. Methylation of <B>1</B> with diazomethane, followed by oxidation with a chromium trioxide-pyridine complex, afforded 12-methoxyabieta-8,12-diene-7,11,14-trione, which on reduction with sodium dithionite gave inuroyleanol.
- 公益社団法人 日本化学会の論文
著者
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Matsumoto Takashi
Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima
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Harada Shogo
Department of Chemistry, Faculty of Science, Hiroshima University
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