Synthesis of Erythrina and Related Alkaloids. XXII. : Intramolecular Cyclization Approach. (1) : New Synthetic Route to Erythrinan and Related Heterocycles and Synthesis of (±)-3-Demethoxy-erythratidinone

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概要

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• Heating of cycloalkanone-2-carboxylate with β-arylethylamine, and oxalylation of the resulting enamino-ester followed by Lewis acid-catalyzed intramolecular cyclization afforded various erythrinan-type heterocycles in excellent yields. This method is widely applicable not only to the synthesis of erythrinans but also to that of A-nor and A-homo analogs and ring-D variants of erythrinan. The alkoxycarbonyl group on the products was readily removed by a new decarbalkoxylation method (heating with magnesium chloride-dimethyl sulfoxide combination). Thus, starting from 2-ethoxycarbonyl-4,4-ethylenedioxy-cyclohexanone, the 2,8-dioxo-erythrinan derivative (35) was synthesized in several steps in high yield, and was readily converted to the natural Erythrina alkaloid, 3-demethoxyerythratidinone.

• 社団法人日本薬学会の論文
• 1990-06-25

著者

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 酒井 由紀

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 礒部 公明

  昭和薬大

• 礒部 公明

  Showa College of Pharmaceutical Sciences

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 佐野 武弘

  Showa College of Pharmaceutical Sciences.

• 中井 章

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 多賀 淳一

  Showa College of Pharmaceutical Sciences

• 津田 喜典

  金沢大薬

• 金子 真理

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 石黒 幸江

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

• 金子 真理

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 多賀 淳一

  Showa College Of Pharmaceutical Sciences:kanazawa University

• 石黒 幸江

  Faculty Of Pharmaceutical Sciences Kanazawa University

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