Cycloaddition Behavior of Cyclopentadienone toward Allylic Alcohols.Formation of Hydrophthalide Derivatives via Internal Addition of Alcohol Group to Bridged Carbonyl of exo [4+2]π Cycloadducts

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概要

• 論文の詳細を見る

• The cycloaddition behavior of 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone (Ia) toward allylic alcohols(II) was investigated. The exo [4+2]π cycloadducts were transformed into hydrophthalide derivatives via intramolecular addition of the alcohol group to the strained bridged carbonyl. The endo [4+2]π cycloadducts underwent transesterification with the bridgehead methoxycarbonyl group to give the lactone derivatives. The structures of the products were determined on the basis of the ^1H- and ^<13>C-NMR spectral data and X-ray analyses. The reactivity of Ia toward allylic alcohols is discussed in terms of frontier molecular orbital (FMO) theory.

• 公益社団法人日本薬学会の論文
• 1993-01-15

著者

• 原野 一誠

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 久野 拓造

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 原野 一誠

  熊本大学 薬

• 原野 一誠

  熊本大学薬学部

• 久野 拓三

  熊本大学薬学部

• 衛藤 仁

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 大屋 倫宏

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 衛藤 仁

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 大屋 倫宏

  Faculty Of Pharmaceutical Sciences Kumamoto University

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