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Title: Concise Construction of the ACDE Ring System of Calyciphylline A Type Alkaloids by a [5+2] Cycloaddition
Authors: Nakamura, Hugh
Kawakami, Manami
Tsukano, Chihiro
Takemoto, Yoshiji
Author's alias: 塚野, 千尋
竹本, 佳司
Keywords: [5+2] cycloaddition
calyciphylline A
daphniphyllum alkaloids
daphniyunnine
synthetic strategy
Issue Date: 2-Jul-2019
Publisher: Wiley
Journal title: Chemistry – A European Journal
Volume: 25
Issue: 37
Start page: 8701
End page: 8704
Abstract: 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.
Rights: 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(Published Version): 10.1002/chem.201901690
PubMed ID: 31063603
Appears in Collections:Journal Articles

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