Studies on Amino Acid Derivatives. IX. : Synthesis of Chiral Penam-3-carboxylic Acid and Its Substituted Derivatives

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概要

• 論文の詳細を見る

• Methyl penam-(3S)-carboxylate (methyl 7-oxo-1-thia-4-azabicyclo[3.2.0]heptane-(3S)-carboxylate), the basic skeleton of penicillin-type β-lactams, has been synthesized from D-cysteine methyl ester and tert-butyl formylacetate in three steps through the formation of the thiazolidinylacetic acid followed by cyclization by Mukaiyama-Ohno's procedure. Use of D-penicillamine methyl ester as well as the dimethyl derivative of tert-butyl formylacetate in the above method provides a general synthetic route to a variety of methyl penam-(3S)-carboxylates having methyl groups at the 2 and/or 6-positions.The yields as well as stereoselectivity at C-5 in the cyclization step are shown to be strongly dependent upon the patterns of substituents on the thiazolidinylacetic acid skeleton, and the reason for this is discussed from the mechanistic viewpoint.

• 社団法人日本薬学会の論文
• 1989-04-25

著者

• 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

• 千葉 卓男

  Pharmaceutical Institute, Tohoku University

• 古谷 利夫

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.,

• 犬飼 紀喜

  Central Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd.,

• 千葉 卓男

  Pharmaceutical Institute Tohoku University

• 古谷 利夫

  Central Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 古谷 利夫

  Tsukuba Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

• 金子 主税

  Pharmaceutical Institute Tohoku University

• 犬飼 紀喜

  Tsukuba Research Laboratories Yamanouchi Pharmaceutical Co. Ltd.

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