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ID 113684
Title Alternative
Asymmetric Total Syntheses and Structure Revisions of Eurotiumide A and Eurotiumide B, and Evaluation of their Fluorescent Properties as Natural Probes
Author
Sato, Hideo Tokushima University
Hayashi, Naoki Kyoto Pharmaceutical University
Oda, Masataka Kyoto Pharmaceutical University
Keywords
natural products
total synthesis
fluorescent probes
Content Type
Journal Article
Description
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.
Journal Title
European Journal of Organic Chemistry
ISSN
10990690
1434193X
NCID
AA1118165X
Publisher
WILEY‐VCH
Volume
2018
Issue
29
Start Page
4013
End Page
4017
Published Date
2018-04-16
Rights
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.
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language
eng
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departments
Pharmaceutical Sciences