Synthesis of (+)-hinokiol, (+)-hinokione, (+)-salviol, and (+)-2-oxoferruginol.
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概要
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Reduction of abieta-5,8,11,13-tetraen-3-one with lithium aluminium hydride afforded the corresponding alcohol, which was submitted to catalytic hydrogenation to yield abieta-8,11,13-trien-3β-ol (<B>7</B>) together with its 5βH-isomer. Acetylation of <B>7</B>, followed by the Friedel-Crafts acylation, afforded 3β-acetoxy-12-acetylabieta-8,11,13-triene. This compound was converted into 3β,12-diacetoxyabieta-8,11,13-triene (<B>11</B>) by the Baeyer-Villiger oxidation. Treatment of <B>11</B> with lithium aluminium hydride yielded hinokiol, which was oxidized to hinokione. Subsequently, hinokiol was methylated and the resulting 12-methyl ether was dehydrated to afford 12-methoxyabieta-2,8,11,13-tetraene. The tetraene was then submitted to hydroboration-oxidation to give 12-methoxyabieta-8,11,13-trien-2α-ol (<B>15</B>) which, on demethylation with ethanethiol and anhydrous aluminium chloride, afforded salviol. Oxidation of <B>15</B> with pyridinium chlorochromate, followed by demethylation, gave 2-oxoferruginol.
- 公益社団法人 日本化学会の論文
著者
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Usui Shuji
Department Of Chemistry Faculty Of Science Hiroshima University
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Mitsuki Masanori
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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Kawashima Hiroyuki
Department of Chemistry, Faculty of Science, Hiroshima University
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Matsumoto Takashi
Department of Applied Material Science, Faculty of Integrated Arts and Science, University of Tokushima
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