Synthesis of (+)-11-hydroxyabieta-2,8,11,13-tetraen-1-one.
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概要
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Treatment of methyl (+)-11-oxo-13β-abieta-8-en-18-oate with copper(II) bromide and lithium bromide afforded the corresponding phenol derivative, which was methylated to methyl 11-methoxyabieta-8,11,13-trien-18-oate (<B>7</B>). The same compound was also prepared from methyl (+)-7,11-dioxo-13β-abieta-8-en-18-oate <I>via</I> methyl 11-hydroxy-7-oxoabieta-8,11,13-trien-18-oate, its methyl ether, and methyl 11-methoxyabieta-6,8,11,13-tetraen-18-oate. The Grignard reaction of <B>7</B> with phenylmagnesium bromide followed by treatment with lead tetraacetate and subsequent oxidation with selenium dioxide afforded 11-methoxy-19-norabieta-4(18),8,11,13-tetraen-3α-ol (<B>12</B>), which was converted to 11-methoxy-19-norabieta-8,11,13-trien-3-one (<B>20</B>) by catalytic hydrogenation, Jones oxidation, and isomerization. The compound <B>20</B> was also obtained by Birch reduction of 11-methoxy-19-norabieta-4,8,11,13-tetraen-3-one prepared from <B>12</B> <I>via</I> 11-methoxy-19-norabieta-4,8,11,13-tetraen-3α-ol. Subsequently, the compound <B>20</B> was transformed to 11-methoxyabieta-1,8,11,13-tetraen-3-one (<B>27</B>) by a series of reactions: acetalization, demethylation, hydrolysis, acetylation, bromination, dehydrobromination, and methylation. Finally, the compound <B>27</B> was converted to the title compound, (+)-11-hydroxyabieta-2,8,11,13-tetraen-1-one (<B>1</B>), by oxidation with alkaline hydrogen peroxide, heating with hydrazine hydrate, Jones oxidation, and demethylation. Although the synthetic (+)-<B>1</B> was shown to be different from natural shonanol, the spectral analyses of the synthetic structural isomers showed the structure of shonanol to be 12-hydroxyabieta-2,8,11,13-tetraen-1-one.
- 公益社団法人 日本化学会の論文
著者
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Imai Sachihiko
Department of Chemistry, Faculty of Science, Hiroshima University
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Yuki Shuhei
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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