Studies toward Total Synthesis of Non-aromatic Erythrina Alkaloids. (1). Synthesis and Isomerization of Unsaturated Bicyclic δ-Lactones

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概要

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• As a model of the C/D ring system of erythroidines, bicyclic unsaturated δ-lactones were synthesized in a regio-selective manner, and their isomerization reaction in the presence of acid, base (DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene), and NaOH were studied. In the lactone form, the 6-ene (3) was the most unstable and isomerized to the 5-ene (1) then to the 1^<(6)>-ene (2). The latter two lactones equilibrate to give ca. 3 : 2 mixture of 1 and 2 in the presence of DBU. On the contrary, in the opened form (NaOH), the lactone 1 was the most unstable and isomerized to 2 and 3. The 1^<(10)>-ene (4) was inert under all of the conditions examined.

• 社団法人日本薬学会の論文
• 1991-11-25

著者

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 毛利 邦彦

  Showa College Of Pharmaceutical Sciences

• 礒部 公明

  Showa College of Pharmaceutical Sciences

• 細井 深造

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 石浦 明子

  Faculty of Pharmaceutical Sciences Kanazawa University

• 高村 佐保

  Faculty of Pharmaceutical Sciences Kanazawa University

• 細井 深造

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 津田 喜典

  金沢大薬

• Mohri K

  Showa College Of Pharmaceutical Sciences

• Isobe K

  Showa College Of Pharmaceutical Sciences

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