Furanosesquiterpenoids: Total synthesis of pallescensins 2, F, and G.
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概要
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Oxidation of the synthetic pallescensin 1 with <I>m</I>-chloroperbenzoic acid, followed by treatment of the resulting epoxide with lithium diethylamide, afforded 3-[2-(2-furyl)ethyl]-4,4-dimethyl-2-methylenecyclohexanol (<B>6</B>). The alcohol <B>6</B> was dehydrated with refluxing hexamethylphosphoric triamide to give pallescensin 2. Oxidation of <B>6</B> with pyridinium chlorochromate, followed by intramolecular cyclization with 85% phosphoric acid, afforded 5,5a,6,7,8,9,9a,10-octahydro-6,6-dimethyl-4<I>H</I>-benzo[5,6]cyclohepta[1,2-<I>b</I>]furan-9-one. This was converted into the corresponding α,β-unsaturated ketone (<B>10</B>) <I>via</I> an α-phenylseleno ketone. Reduction of <B>10</B> with lithium aluminium hydride, followed by dehydration with hexamethylphosphoric triamide at 200–210 °C, afforded pallescensin G, which was further isomerized to pallescensin F.
- 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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Matsumoto Takashi
Department of Applied Material Science, Faculty of Integrated Arts and Science, University of Tokushima
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