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Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone
http://hdl.handle.net/10228/00008086
http://hdl.handle.net/10228/00008086a72affcc-eb39-4e00-9abc-dee2fd884c39
名前 / ファイル | ライセンス | アクション |
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Item type | 学術雑誌論文 = Journal Article(1) | |||||||||
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公開日 | 2021-03-19 | |||||||||
タイトル | ||||||||||
タイトル | Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone | |||||||||
言語 | ||||||||||
言語 | eng | |||||||||
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 |
Othman, Dina I. A.
× Othman, Dina I. A.× Otsuka, Kota× Takahashi, Shuhei× Selim, Khalid B.× El-Sayed, Magda A.× Tantawy, Atif S.× Okauchi, Tatsuo
WEKO
880
× Kitamura, Mitsuru
WEKO
19669
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抄録 | ||||||||||
内容記述タイプ | Abstract | |||||||||
内容記述 | The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-catalyzed intramolecular cyclization reaction of the corresponding diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs–Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag2O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A. | |||||||||
書誌情報 |
Synlett 巻 29, 号 4, p. 457-462, 発行日 2017-11-03 |
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出版者 | ||||||||||
出版者 | Georg Thieme Verlag KG | |||||||||
ISSN | ||||||||||
収録物識別子タイプ | ISSN | |||||||||
収録物識別子 | 0936-5214 | |||||||||
ISSN | ||||||||||
収録物識別子タイプ | ISSN | |||||||||
収録物識別子 | 1437-2096 | |||||||||
DOI | ||||||||||
関連タイプ | isVersionOf | |||||||||
識別子タイプ | DOI | |||||||||
関連識別子 | https://doi.org/10.1055/s-0036-1589118 | |||||||||
キーワード | ||||||||||
主題Scheme | Other | |||||||||
主題 | diazonapthoquinone - rhodium - eleutherol - eleuthoside A - glycosidation - intramolecular cyclization - 1 Introduction - 2 Results and Discussion - 2.1 Synthetic Strategy - 2.2 Synthesis of Aglycone | |||||||||
キーワード | ||||||||||
主題Scheme | Other | |||||||||
主題 | Eleutherol - 2.3 Glycosidation and Synthesis of Eleuthoside A - 3 Conclusions | |||||||||
日本十進分類法 | ||||||||||
主題Scheme | NDC | |||||||||
主題 | 434 | |||||||||
権利 | ||||||||||
権利情報 | Copyright (c) Georg Thieme Verlag Stuttgart· New York | |||||||||
版 | ||||||||||
出版タイプ | AM | |||||||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||||||
査読の有無 | ||||||||||
値 | yes | |||||||||
研究者情報 | ||||||||||
https://hyokadb02.jimu.kyutech.ac.jp/html/103_ja.html | ||||||||||
連携ID | ||||||||||
8612 |