Asymmetric Total Syntheses and Structure Revision of Eurotiumide A and B, and Evaluation of their Fluorescent Properties as Natural Probes

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  • Nakayama Atsushi
    Institutes of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University

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  • 天然物全合成から見つけた蛍光化合物—Eurotiumide類の不斉全合成と蛍光特性—
  • 天然物全合成から見つけた蛍光化合物 : Eurotiumide類の不斉全合成と蛍光特性
  • テンネンブツ ゼン ゴウセイ カラ ミツケタ ケイコウ カゴウブツ : Eurotiumideルイ ノ フセイ ゼン ゴウセイ ト ケイコウ トクセイ

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<p>Asymmetric total syntheses and structure revision of dihydroisocoumarin-type natural products, eurotiumide A and eurotiumide B have been described. Key features of these total syntheses are the asymmetric Shi epoxidation, regioselective epoxide opening, and Pd-catalyzed CO insertion-lactonization cascade reaction to construct 4-methoxyisochroman-1-one skeleton. X-ray crystallographic analysis of the key intermediate revealed the absolute configuration and relative structure of eurotiumides, and it revised the reported structures of eurotiumide A and B, respectively. These natural products also exhibited highly fluorescence with several solvents with large Stokes shift.</p>

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