An Efficient and Practical Synthesis of Bicyclo[3.3.1]nonane-2,4-diones(Organic,Chemical)

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概要

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• Cyclohexane-1,3-dicarboxylic anhydrides (IVa-c), prepared from isophthalic acids in several steps, were treated with diethyl magnesiomalonate and triethylamine to give 3-di(ethoxycarbonyl)-acetylcyclohexanecarboxylic acids (Va-c) in good yields. Compounds Va-c were converted into methyl 3-acetylcyclohexanecarboxylates (VIa-c) by decarboxylation and esterification. Cyelization of Via-c to bicyclo[3.3.1]nonane-2,4-diones (I) was performed by refluxing a mixture of VI and potassium hydride in xylene. In the case of VIb, two products (Id and Ie) were obtained. Compounds Ic and Ie were hydrolyzed to Ib and Ig, respectively, by treatment with p-toluenesulfonic acid in acetone and phosphorus tribromide. The 7α-hydroxy β-diketone (If) was obtained from Ib-triketal in three steps via reduction of Ib-2,4-diketal with lithium aluminum hydride. The keto-enol equilibrium of these β-diketones (Ia-f) and 9-substituted bicyclo[3.3.1]-nonane-2,4-diones (Xa-b) in deuteriochloroform is also described.

• 公益社団法人日本薬学会の論文
• 1987-08-25

著者

• Muraoka Osamu

  Faculty Of Pharmaceutical Sciences Kinki University

• MOMOSE TAKEFUMI

  Faculty of Pharmaceutical Sciences, Kinki University

• Yamazaki T

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• YAMAZAKI TAKAO

  Faculty of Pharmaceutical Sciences, Tayama Medical & Pharmaceutical University

• Momose Takefumi

  Faculty Of Pharmaceutical Sciences Kinki University

• Muraoka Osamu

  Faculty Of Phamaceutical Sciences Kinki University

• MATOBA KATSUHIDE

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• ITOOKA TOSHIYUKI

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• CHINTANI MASARU

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• Matoba K

  Toyama Medical & Pharmaceutical Univ. Toyama Jpn

• Yamazaki Takao

  Faculty Of Engineering Shinshu University

• Chintani Masaru

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• Itooka T

  Kinki Univ. Osaka Jpn

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