Concise Construction of the ACDE Ring System of Calyciphylline A Type Alkaloids by a [5+2] Cycloaddition

• 塚野, 千尋

  Graduate School of Pharmaceutical Sciences, Kyoto University

• 竹本, 佳司

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Tsukano, Chihiro

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Takemoto, Yoshiji

  Graduate School of Pharmaceutical Sciences, Kyoto University

抄録

A concise route for construction of the ACDE ring skeleton in calyciphylline A type alkaloids was developed using an intramolecular [5+2] cycloaddition reaction of an oxidopyrylium species bearing a tetrasubstituted olefin. Key to the success of this reaction was the combination of acid and base, which accelerated the construction of this skeleton containing a spiro ring and vicinal quaternary carbon centers. The resultant tricyclic ADE ring compound was converted to an ACDE ring model through C−H oxidation and an aza‐Wittig reaction.

収録刊行物

• Chemistry - A European Journal

  Chemistry - A European Journal 25 (37), 8701-8704, 2019-07-02

  Wiley

キーワード

• [5+2] cycloaddition
• calyciphylline A
• daphniphyllum alkaloids
• daphniyunnine
• synthetic strategy

詳細情報

• CRID: 1050282813382951808
• NII論文ID: 120006708212
• NII書誌ID: AA11076269
• ISSN: 09476539
• ISSN: 15213765
• DOI: 10.1002/chem.201901690
• HANDLE: 2433/243179
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201901690
• Web Site: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.201901690
• 本文言語コード: en
• 資料種別: journal article
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