Synthesis in the Diazasteroid Group. XX. Synthesis of the 5,14-Diazasteroid System(Organic,Chemical)

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概要

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• trans-2-Quinolizidinone (I) was treated with methyl 2-pyrrolidylacetate (III) to give a mixture of two isomers, 5,14-diaza-1,6-cyclo-1,10-secogon-8-en-11-one (IV) and 5,14-diazagon-8-en-11-one (Va) in 8.6 and 2.7% yields, respectively. 1,2,3,3a,4,5,6,7,8,9-Decahydro-7-benzoylpyrrolo[1,2-α]-[1,6]-naphthyridin-5-one (VIb) [prepared from 1-benzoyl-4-piperidone (IIb) and III] was hydrolyzed and then allowed to react with methyl vinyl ketone to give a Michael adduct (VId). It was treated with mercuric acetate to afford regio- and stereoselectively 5,14-diazagon-8-ene-2,11-dione (Vb), whose angular protons at the C_<10> and C_<13> were anti to each other. The structure of Vb was determined by X-ray crystallographic analysis. Compound Vb was converted to Va via a thioketai (Vc).

• 社団法人日本薬学会の論文
• 1987-01-25

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

• 永田 正典

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• 山崎 高應

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 平井 美朗

  Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

• 時沢 実

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• 涌井 優子

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Osaka University

• 平井 美朗

  富山医科薬科大学薬学部

• 平井 美朗

  Pharmaceutical Institute Tohoku University

• 平井 美朗

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 涌井 優子

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• 時沢 実

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

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