63 分子内閉環による7α-メトキシ-1-オキサセフェム骨格の新しい立体制御的合成

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概要

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• A new, short-step synthesis of 7β-benzoylamino-7α-methoxy-3-methyl- and 3-substituted-methyl-1-oxacephem-4-carboxylates 13 via glycols 6 and halohydrins 11 is described. Oxidation of epioxazoline 5 with OsO_4-KClO_3, NBS, or trichloroisocyanuric acid gave a diastereoisomeric mixture of the diols 6 or halohydrins 11. The hydroxy derivatives were cyclised to the 1-oxacephams 7 and 12 by intramolecular stereospecific etherification catalyzed with a Lwis acid. Treatment of 1-oxacephams 7 and 12 with a dehydrating agent (SOCl_2-Py) or a base (DBU) gave the 1-oxacephems 8, which were methoxylated at C_7 by the usual method (t-BuOCl-LiOCH_3). The side chain cleavage of the methoxy amides 13 was effected without epimerization at C_7 by the method reported by us previously.

• 天然有機化合物討論会の論文
• 1979-09-20

著者

• 鎌田 進

  塩野義研

• 永田 亘

  塩野義製薬株式会社研究所

• 吉岡 美鶴

  塩野義製薬株式会社研究所

• 青木 務

  塩野義研

• 吉岡 美鶴

  塩野義研

• 上尾 庄一郎

  塩野義研

• 鴻池 敏郎

  塩野義研

• 仙藤 宥二

  塩野義研

• 永田 亘

  塩野義研

• 鴻池 敏郎

  Shionogi Research Laboratories Shionogi & Co. Ltd.

• 上尾 庄一郎

  Shionogi Research Laboratories Shionogi & Co. Ltd.

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