Reduction of Vinylogous Thioesters with Lithium Aluminum Hydride. II. Reduction of 2-Methyl-3-phenylthio-5-substituted-2-cyclopentenones

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概要

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• 2,5-Dimethyl-3-phenylthio-2-cyclopentenone (IIb) and 5-tert-butyl-2-methyl-3-phenylthio-2-cyclopentenone (IIc) were reduced with an excess of lithium aluminum hydride (LAH) in ether to give quantitatively the corresponding 1,2-addition products, 2,5-dimethyl-3-phenylthio-2-cyclopentenol (IIIb) and 5-tert-butyl-2-methyl-3-phenylthio-2-cyclopentenol (IIIc), respectively. Compound IIIb was transformed into the vinylsulfide (IVb) and the enone (Vb) on standing at room temperature, whereas IIIc was transformed into the diene (VII). 5-tert-Butyl-2-methyl-3-phenoxy-2-cyclopentenone (IX) gave 3-tert-butyl-1-methyl-5-phenoxycyclopentene (XI) in 63.1% yield on reduction with LAH in ether.

• 社団法人日本薬学会の論文
• 1985-07-25

著者

• 山崎 高應

  Faculty of Pharmaceutical Sciences, University of Toyama

• 的場 勝英

  Faculty of Pharmaceutical Sciences, University of Toyama

• 山崎 高広

  富山医科薬科大学

• 山崎 高應

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 森田 多賀史

  Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Osaka University

• 森田 多賀史

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

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