1,6-Asymmetric Induction Utilizing Asymmetric Desymmetrization by Diastereoselective C-O Bond Fission of the 4-Substituted Bicyclic Acetal : Application to a Synthesis of (-)-Frontalin

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概要

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• 1,6-Asymmetric induction was achieved in the acid-induced diastereoselective acetal cleavage reaction of a 4-substituted bicyclic acetal 8 bearing a chiral sulfinyl group. On treatment with titanium tetrachloride and 2,6-disubstituted pyridine bases, 8 gave a synthetically versatile 3,3-disubstituted dihydropyran derivative 9a with moderate diastereoselectivity. The utility of this chiral synthon was successfully demonstrated by a formal synthesis of (-)-frontalin.

• 公益社団法人日本薬学会の論文
• 1998-02-15

著者

• 今西 武

  大阪大学大学院薬学研究科

• 岩田 宙造

  阪大院薬

• Tanaka T

  Kvushu Univ. Fukuoka Jpn

• Tanaka T

  Osaka Univ. Osaka Jpn

• IWATA Chuzo

  Faculty of Pharmaceutical Sciences, Osaka University

• Iwata Chuzo

  Faculty Of Pharmaceutical Sciences Osaka University

• Tokuno K

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 恒雄

  Department Of Pharmacy Hyogo College Of Medicine

• 高橋 以都美

  Faculty Of Pharmaceutical Sciences Osaka University

• Tanaka Tetsuaki

  Faculty Of Pharmaceutical Sciences Osaka University

• MAEZAKI Naoyoshi

  Faculty of Pharmaceutical Sciences, Osaka University

• Maezaki Naoyoshi

  Faculty Of Pharmaceutical Sciences Osaka University

• Imanishi Takeshi

  Graduate Shool Of Pharmaceutical Sciences Osaka University

• 正垣 武志

  Research Department Sawai Pharmaceutical Co. Ltd.

• SHOGAKI Takeshi

  Faculty of Pharmaceutical Sciences, Osaka University

• TOKUNO Katsuya

  Faculty of Pharmaceutical Sciences, Osaka University

• Uchida Mihoko

  Department Of Biochemistry Faculty Of Pharmaceutical Sciences Hoshi University

• UCHIDA Masashi

  Faculty of Pharmaceutical Sciences, Osaka University

• IMAMURA Tsuneaki

  Faculty of Pharmaceutical Sciences, Osaka University

• Uchida Masashi

  Faculty Of Pharmaceutical Sciences Osaka University

• Imamura T

  Faculty Of Pharmaceutical Sciences Osaka University

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