Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XVIII. : Synthesis of Azetidin-2-ones from 1,3-Dioxin-4-ones via 3-Hydroxycarboxamides

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概要

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• A general method for the synthesis of azetidin-2-ones from 1,3-dioxin-4-ones is described. The method consists of 1) the formatin of β-ketocarboxamides, 2) their reduction to 3-hydroxycarboxamides, 3) mesylationg, and 4) base-mediated cyclization of 3-mesyloxycarboxamides to the final azetidinones. Stereochemical demand in the cyclizatino step has been clarified by using 5,6-tri- and -tetramethylene derivatives of 2,2-dimethyl-1,3-dioxin-4-one. Microbiological reduction of the acetoacetamides by baker's yeast gave (S)-3-hydroxybutanamides of ≥98% optical purity, whose cyclization afforded (R)-4-methylazetidin-2-ones.

• 社団法人日本薬学会の論文
• 1989-11-25

著者

• 佐藤 雅之

  静岡県立大学薬学部

• 小林 聡

  Pharmaceutical Institute Tohoku University

• 榊 潤一

  Pharmaceutical Institute Tohoku University

• 金子 主税

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 金子 主税

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• 佐藤 雅之

  Pharmaceutical Institute, Tohoku University

• 金子 主税

  Pharmaceutical Institute Tohoku University

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