アクセス数 : ?
ダウンロード数 : ?
ID 113684
タイトル別表記
Asymmetric Total Syntheses and Structure Revisions of Eurotiumide A and Eurotiumide B, and Evaluation of their Fluorescent Properties as Natural Probes
著者
Sato, Hideo Tokushima University
Hayashi, Naoki Kyoto Pharmaceutical University
Oda, Masataka Kyoto Pharmaceutical University
キーワード
natural products
total synthesis
fluorescent probes
資料タイプ
学術雑誌論文
抄録
Asymmetric total syntheses and structure revisions of dihydroisocoumarin-type natural products, eurotiumide A and eurotiumide B have been described. The key features of these total syntheses are the asymmetric Shi epoxidation, regio and stereo-selective epoxide opening, C1 insertion/lactonization cascade reaction for constructing 4-methoxyisochroman-1-one skeleton. We confirmed the structures and configurations of eurotiumide A and B on the basis of X-ray crystallographic analysis of the key intermediate, and revealed that eurotiumide A and B have cis and trans configurations at H3/H4 positions, which are the opposite relationship of the stereochemistry from the previous report, respectively. The absolute configurations of them are also determined. These natural products exhibited highly fluorescence in several solvents with large Stokes shifts involving the excited-state intramolecular proton transfer mechanism, which is supported by time-dependent density functional theory. Eurotiumide A also emitted fluorescence in Bacillus cereus.
掲載誌名
European Journal of Organic Chemistry
ISSN
10990690
1434193X
cat書誌ID
AA1118165X
出版者
WILEY‐VCH
2018
29
開始ページ
4013
終了ページ
4017
発行日
2018-04-16
権利情報
This is the peer-reviewed version of the following article: Nakayama, A. , Sato, H. , Karanjit, S. , Hayashi, N. , Oda, M. and Namba, K. (2018), Asymmetric Total Syntheses and Structure Revisions of Eurotiumide A and Eurotiumide B, and Their Evaluation as Natural Fluorescent Probes. Eur. J. Org. Chem., 2018: 4013-4017, which has been published in final form at https://doi.org/10.1002/ejoc.201800535. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving.
EDB ID
出版社版DOI
出版社版URL
フルテキストファイル
言語
eng
著者版フラグ
著者版
部局
薬学系