Synthetic Photochemistry. LVII. Facile Photochemical Construction of Hexahydro-as-indacene Skeleton, a Carbon Framework of Ikarugamycin, from High-Pressure Diels-Alder Adducts of Tropones-Cyclopentenone.
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概要
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The high-pressure Diels–Alder reaction of tropones with 2–cyclopenten-1-one afforded isomeric mixtures of adducts. Upon UV irradiation, these adducts isomerized to hexahydro-<I>as</I>-indacene, via [1,3] acyl migration, and tetracyclo[7.3.0.0<SUP>3,7</SUP>.0<SUP>6,8</SUP>]undecene derivatives through a ketene intermediate via a di-π-methane rearrangement. The former tricyclic system corresponds to the carbon skeleton of ikarugamycin. An "<I>exo</I> [6+4] adduct" of tropone and 1,4-cyclopentadien-1-ol, an enol form of 2-cyclopentenone, was obtained as a by-product.
- 公益社団法人 日本化学会の論文
著者
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KATO Nobuo
Institute of Advanced Material Study, 86 Kyushu University
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Mori Akira
Institute For Materials Chemistry And Engineering Kyushu University
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Li Zhi-Hong
Graduate School of Engineering Sciences, 39, Kyushu University
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Kato Nobuo
Institute of Advanced Material Study, 86, Kyushu University
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Takeshita Hitoshi
Graduate School of Engineering Sciences, 39, Kyushu University
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