1,6-Dihydro-3 (2H)-pyridinones. X. 2-Azabicyclo [2.2.2] octane Ring Formation via Intramolecular Michael Reaction : Total Synthesis of (±)-Ibogamine and (±)-Epiibogamine

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概要

• 論文の詳細を見る

• A new elaboration method for the 2-azabicyclo [2.2.2] octane ring via an intramolecular Michael reaction has been developed and applied to the total synthesis of (±)-ibogamine (1) and (±)-epiibogamine (2). The unsaturated ester (9) derived from ethyl 1,6-dihydro-3 (2H)-pyridinone-1-carboxylate (3a) was reacted with potassium carbonate or sodium hydride to provide two 2-azabicyclo [2.2.2] octanone derivatives (19 and 20), the stereochemistry of which was confirmed by chemical evidence. By a three-step sequence, the esters (19 and 20) were converted into 27 and 36,which were then transformed into the corresponding amides (31 and 40). Cyclization of 31 and 40 followed by reduction with a complex of lithium aluminum hydride-aluminum chloride furnished (±)-epiibogamine (2) and (±)-ibogamine (1), respectively, in good yields.

• 公益社団法人日本薬学会の論文
• 1985-10-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 八木 典幸

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 花岡 美代次

  金沢大学薬学部

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

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