Synthetic Studies of Carbapenem and Penem Antibiotics. I. Facile Synthesis of a Key Intermediate : 4-Acetoxy-3-(1-hydroxyethyl)-2-azetidinone

スポンサーリンク

概要

• 論文の詳細を見る

• A highly efficient synthesis of(3R, 4R)-4-acetoxy-3-[(R)-1-hydroxyethyl]-2-azetidinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, was accomplished. It was found that oxymercuration-reduction of easily obtainable 4-alkyloxycarbonyl-1-(di-p-anisylmetyl)-3-ethenyl-2-azetidinone could be employed as a key stereoselective reaction. The chiral starting material was obtained by optical resolution or asymmetric (2+2) cycloaddition. The desired product was afforded in four steps, that is, oxymercuration-reduction, oxidative decarboxylation, protection of the hydroxy group and removal of the N-protecting group.

• 公益社団法人日本薬学会の論文
• 1991-08-25

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

• 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.,

• 榎本 正夫

  Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd.,

• 井上 孝明

  Research Laboratories Sumitomo Pharmaceuticals Co. Ltd.

• 榎本 正夫

  Research Laboratories Sumitomo Pharmaceuticals Co. Ltd.

• 松村 春記

  Development Research Laboratories I Sumitomo Pharmaceuticals Research Center

関連論文

• Stability of a 1β-Methylcarbapenem Antibiotic, Meropenem (SM-7338) in Aqueous Solution
• The Stability of a Novel Carbapenem Antibiotic, Meropenem (SM-7338), in a Solid State Formulation for Injection
• 34 化学シフト予測法を用いるオリゴ糖と超分子の立体配座解析(口頭発表の部)
• 67 光学活性カルバペネム鍵合成中間体の合成研究(口頭発表の部)
• カルバペネム化学の最近の進歩
• 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
• Dibenzotetracyclic Derivatives. II. Synthesis of 9-Aminoalkyl-9,10-dihydro-9,10-methanoanthracenes
• Dibenzotetracyclic Derivatives. III. Synthesis of 9-γ-Methylaminopropyl-9,10-dihydro-9,10-propanoanthracene
• 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

もっと見る 閉じる

スポンサーリンク