| アイテムタイプ |
文献 / Documents(1) |
| 公開日 |
2019-09-18 |
| アクセス権 |
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アクセス権 |
open access |
| 資源タイプ |
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資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
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資源タイプ |
journal article |
| 出版社版DOI |
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関連識別子 |
https://doi.org/10.1002/ejoc.201800535 |
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関連名称 |
10.1002/ejoc.201800535 |
| 出版タイプ |
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出版タイプ |
AM |
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出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
| タイトル |
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タイトル |
Asymmetric Total Syntheses and Structure Revisions of Eurotiumide A and Eurotiumide B, and Their Evaluation as Natural Fluorescent Probes |
| タイトル別表記 |
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その他のタイトル |
Asymmetric Total Syntheses and Structure Revisions of Eurotiumide A and Eurotiumide B, and Evaluation of their Fluorescent Properties as Natural Probes |
| 著者 |
中山, 淳
サトウ, ヒデオ
カランジット, サンギータ
ハヤシ, ナオキ
オダ, マサタカ
難波, 康祐
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| 抄録 |
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内容記述 |
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. |
| キーワード |
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主題 |
natural products |
| キーワード |
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主題 |
total synthesis |
| キーワード |
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主題 |
fluorescent probes |
| 書誌情報 |
en : European Journal of Organic Chemistry
巻 2018,
号 29,
p. 4013-4017,
発行日 2018-04-16
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収録物識別子タイプ |
ISSN |
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収録物識別子 |
10990690 |
| 収録物ID |
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収録物識別子タイプ |
ISSN |
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収録物識別子 |
1434193X |
| 収録物ID |
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収録物識別子タイプ |
NCID |
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収録物識別子 |
AA1118165X |
| 出版者 |
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出版者 |
WILEY‐VCH |
| 権利情報 |
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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. |
| EID |
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識別子 |
342431 |
| 言語 |
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言語 |
eng |
ejoc_2018_29_4013.pdf (1.33 MB)
