Synthetic Studies of Carbapenem and Penem Antibiotics. IV. Stereoselective Reduction of 3-Acetyl-2-azetidinone with Aminoalkoxyborane

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概要

• 論文の詳細を見る

• The transformation of 3-acetyl-2-azetidinone into 3-[(R)-1-hydroxyethyl]-2-azetidinone was achieved by highly stereoselective reduction with N-benzylaminoethoxyborane in the presence of trifluoroborane etherate. The combination of this reduction method and optical resolution using l-norephedrine provides a practical synthetic method for (3S, 4S)-4-carboxy-1-(di-p-anisylmethyl)-3-[(R)-1-hydroxyethyl]-2-azetidinone, which is a key intermediate in the synthesis of carbapenem and penem antibiotics.

• 公益社団法人日本薬学会の論文
• 1992-11-25

著者

• 砂川 洵

  Research Center, Sumitomo Pharmaceuticals Co., Ltd.,

• 佐々木 章

  住友製薬(株)総合研究所

• 砂川 洵

  住友製薬総合研究所

• 砂川 洵

  Research Center Sumitomo Pharmaceuticals Co. Ltd.

• 松村 春記

  Development Research Laboratories I, Sumitomo Pharmaceuticals Research Center

• 矢野 恒夫

  Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd.,

• 高田 真治

  Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd.,

• 井上 孝明

  Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd.,

• 佐々木 章

  Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd.,

• 松村 春記

  Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd.,

• 矢野 恒夫

  Research Laboratories Sumitomo Pharmaceuticals Co. Ltd.

• 高田 真治

  Research Laboratories Sumitomo Pharmaceuticals Co. Ltd.

• 井上 孝明

  Research Laboratories Sumitomo Pharmaceuticals Co. Ltd.

• 松村 春記

  Development Research Laboratories I Sumitomo Pharmaceuticals Research Center

関連論文

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• Synthetic Studies of Carbapenem and Penem Antibiotics. V. Efficient Synthesis of the 1β-Methylcarbapenem Skeleton
• Synthetic Studies of Carbapenem and Penem Antibiotics. IV. Stereoselective Reduction of 3-Acetyl-2-azetidinone with Aminoalkoxyborane
• Synthetic Studies of Carbapenem and Penem Antibiotics. III. A Synthesis of a Key Intermediate for 1β-Methylcarbapenem
• Synthetic Studies of Carbapenem and Penem Antibiotics. II. Synthesis of 3-Acetyl-2-azetidinones by (2+2) Cycloaddition of Diketene and Schiff Bases
• カルバペネム抗生物質の開発
• Synthetic Studies of Carbapenem and Penem Antibiotics. I. Facile Synthesis of a Key Intermediate : 4-Acetoxy-3-(1-hydroxyethyl)-2-azetidinone
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• Studies of Cyclodextrin Inclusion Complexes. II. Application of the Partition Coefficient Method
• Studies of Cyclodextrin Inclusion Complexes. I. Complex between Cyclodextrins and Bencyclane in Aqueous Solution
• Synthetic Studies of Carbapenem and Penem Antibiotics. VI. Stereoselective Reduction of Enamino Ketone and Lactonization of the Reduction Product for the Synthesis of 1β-Methylcarbapenem

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