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タイトル: | Concise Construction of the ACDE Ring System of Calyciphylline A Type Alkaloids by a [5+2] Cycloaddition |
著者: | Nakamura, Hugh Kawakami, Manami Tsukano, Chihiro https://orcid.org/0000-0002-9361-0857 (unconfirmed) Takemoto, Yoshiji https://orcid.org/0000-0003-1375-3821 (unconfirmed) |
著者名の別形: | 塚野, 千尋 竹本, 佳司 |
キーワード: | [5+2] cycloaddition calyciphylline A daphniphyllum alkaloids daphniyunnine synthetic strategy |
発行日: | 2-Jul-2019 |
出版者: | Wiley |
誌名: | Chemistry - A European Journal |
巻: | 25 |
号: | 37 |
開始ページ: | 8701 |
終了ページ: | 8704 |
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. |
著作権等: | This is the peer reviewed version of the following article: H. Nakamura, M. Kawakami, C. Tsukano, Y. Takemoto, Chem. Eur. J. 2019, 25, 8701., which has been published in final form at https://doi.org/10.1002/chem.201901690. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. The full-text file will be made open to the public on 2 July 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 |
URI: | http://hdl.handle.net/2433/243179 |
DOI(出版社版): | 10.1002/chem.201901690 |
PubMed ID: | 31063603 |
出現コレクション: | 学術雑誌掲載論文等 |
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