Structure and synthesis of (+)-shonanol.
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概要
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The structure of shonanol was restudied and found to be 12-hydroxyabieta-2,8,11,13-tetraen-1-one (<B>1</B>) by the following synthesis. A Grignard reaction of methyl (+)-12-methoxyabieta-8,11,13-trien-18-oate with phenylmagnesium bromide, followed by treatment with lead tetraacetate and calcium carbonate afforded a mixture of <I>Δ</I><SUP>3<SUB>−</SUB></SUP>, <I>Δ</I><SUP>4<SUB>−</SUB></SUP>, and <I>Δ</I><SUP>4(18)</SUP>-19-nor compounds. This was oxidized with selenium dioxide to give (+)-12-methoxy19-norabieta-4(18),8,11,13-tetraen-3α-ol. This alcohol was converted to (+)-12-methoxyabieta-5,8,11,13-tetraen-3-one (<B>6</B>) by the known procedure. Reduction of <B>6</B> with lithium aluminium hydride, followed by catalytic hydrogenation, yielded (+)-12-methoxyabieta-8,11,13-trien-3β-ol (<B>8</B>) and a small amount of its <I>cis</I> isomer. The compound (<B>8</B>) was then converted to (+)-12-methoxyabieta-1,8,11,13-tetraen-3-one (<B>12</B>) by a series of reactions: oxidation with pyridinium chlorochromate, bromination with pyridinium tribromide, and dehydrobromination with lithium carbonate and lithium bromide. Demethylation of <B>12</B> with boron tribromide gave (+)-12-hydroxyabieta-1,8,11,13-tetraen-3-one. Oxidation of <B>12</B> with alkaline hydrogen peroxide, followed by treatment with hydrazine hydrate, gave (+)-12-methoxyabieta-2,8,11,13-tetraen-1α-ol; this was oxidized with Jones reagent to give the corresponding 1-oxo compound. The 1-oxo compound was finally demethylated with boron tribromide to yield (+)-<B>1</B>, whose spectra were identical with those of natural shonanol.
- 公益社団法人 日本化学会の論文
著者
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Kawashima Hiroyuki
Department Of Medicinal Chemistry Kyoto Pharmaceutical University
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Imai Sachihiko
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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