WEKO3
アイテム
Structural Revision and Biomimetic Synthesis of Goupiolone?B
http://hdl.handle.net/10069/37836
http://hdl.handle.net/10069/37836ebf33498-3488-42c6-9147-32044a09dc00
名前 / ファイル | ライセンス | アクション |
---|---|---|
ACIE56_11855.pdf (243.6 kB)
|
|
Item type | 学術雑誌論文 / Journal Article(1) | |||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
公開日 | 2018-09-18 | |||||||||||||
タイトル | ||||||||||||||
タイトル | Structural Revision and Biomimetic Synthesis of Goupiolone?B | |||||||||||||
言語 | ||||||||||||||
言語 | eng | |||||||||||||
キーワード | ||||||||||||||
主題Scheme | Other | |||||||||||||
主題 | natural products | |||||||||||||
キーワード | ||||||||||||||
主題Scheme | Other | |||||||||||||
主題 | biomimetic synthesis | |||||||||||||
キーワード | ||||||||||||||
主題Scheme | Other | |||||||||||||
主題 | structure elucidation | |||||||||||||
キーワード | ||||||||||||||
主題Scheme | Other | |||||||||||||
主題 | oxidation | |||||||||||||
キーワード | ||||||||||||||
主題Scheme | Other | |||||||||||||
主題 | rearrangement | |||||||||||||
資源タイプ | ||||||||||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||||||||||
資源タイプ | journal article | |||||||||||||
著者 |
Matsuo, Yosuke
× Matsuo, Yosuke
× Yoshida, Ayane
× Saito, Yoshinori
× Tanaka, Takashi
|
|||||||||||||
抄録 | ||||||||||||||
内容記述タイプ | Abstract | |||||||||||||
内容記述 | Goupiolones?A and B are unique phenolic compounds with significant DNA-damaging activity. In this study, the structure of goupiolone?B was revised on the basis of DFT calculations of the 13C?NMR chemical shifts and biosynthetic considerations. The dibenzobicyclo[3.2.2]nonane skeleton of the revised structure suggested that goupiolone?B was produced by oxidative coupling between catechol and goupiolone?A, which was strongly supported by biomimetic synthesis. Furthermore, racemization of goupiolone?B was observed during the attempted resolution of its racemic mixture. A plausible racemization mechanism involving α-ketol rearrangement is proposed. | |||||||||||||
書誌情報 |
Angewandte Chemie International Edition 巻 56, 号 39, p. 11855-11859, 発行日 2017-09-18 |
|||||||||||||
出版者 | ||||||||||||||
出版者 | Wiley-VCH Verlag GmbH & Co. KGaA | |||||||||||||
ISSN | ||||||||||||||
収録物識別子タイプ | ISSN | |||||||||||||
収録物識別子 | 14337851 | |||||||||||||
DOI | ||||||||||||||
関連タイプ | isVersionOf | |||||||||||||
識別子タイプ | DOI | |||||||||||||
関連識別子 | 10.1002/anie.201706532 | |||||||||||||
権利 | ||||||||||||||
権利情報 | c 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim | |||||||||||||
権利 | ||||||||||||||
権利情報 | This is the accepted version of the following article: Angewandte Chemie - International Edition, 56(39), pp.11855-11859; 2017, which has been published in final form at http://dx.doi.org/10.1002/anie.201706532 This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy http://olabout.wiley.com/WileyCDA/Section/id-820227.html | |||||||||||||
著者版フラグ | ||||||||||||||
出版タイプ | AM | |||||||||||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||||||||||
引用 | ||||||||||||||
内容記述タイプ | Other | |||||||||||||
内容記述 | Angewandte Chemie International Edition, 56(39), pp.11855-11859; 2017 |