Hofmann Degradations of Tetrahydrosecurinine and Tetrahydrosecurininol. Stereochemistry at C-3a of Tetrahydrosecurinine

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概要

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• The Hofmann degradations of tetrahydrosecurinine (II) and tetrahydrosecurininol (III) resulted in N-C_<5a> ring opening. The former gave two products, a normal methine base (VII) and an abnormal product (VIII), and the latter gave a normal methine base (XIII) alone. These products, (VII), (VIII), and (XIII), were interrelated as follows. Dehydration of VIII followed by hydrogenation gave an amino-lactone (IX), which was also prepared from VII by hydrogenation. On the other hand, lithium aluminum hydride reduction of VII gave XIII, which was converted to an amino-diol (XIV) by hydrogenation. The syntheses of the racemates of IX and XIV provided the proofs for their structures. The result establishes the configuration at C_<3a> of II.

• 社団法人日本薬学会の論文
• 1965-01-25

著者

• 田村 恭光

  Faculty Of Pharmaceutical Sciences Osaka University

• 堀井 善一

  Faculty Of Pharmaceutical Sciences Josai University

• 池田 正澄

  Faculty of Pharmaceutical Sciences, Osaka University

• 花岡 美代次

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 斉藤 清一

  田辺製薬研

• 重松 暹

  田辺製薬研

• 斎藤 清一

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 斎藤 清一

  Osaka Research Laboratory, Gohei Tanabe & Co., Ltd.

• 山脇 泰彦

  Faculty of Pharmaceutical Sciences, Osaka University

• 重松 暹

  Osaka Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 小寺 啓司

  Osaka Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 重松 暹

  Osaka Research Laboratory Tanabe Seiyaku Co. Ltd.

• 堀井 善一

  Faculty Of Pharmaceutical Sciences Osaka University

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