國家衛生研究院 NHRI:Item 3990099045/5787
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    題名: The first total synthesis of cytopiloyne, an anti-diabetic, polyacetylenic glucoside
    作者: Kumar, CR;Tsai, CH;Chao, YS;Lee, JC
    貢獻者: Institute of Biotechnology and Pharmaceutical Research
    摘要: The first total synthesis of cytopiloyne 1, a novel bioactive polyacetylenic glucoside isolated from the extract of Bidens pilosa, is described. The structure of cytopiloyne was determined to be 2-beta-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetrayne by using various spectroscopic methods, but the chirality of the polyyne moiety was unknown. Herein, the convergent synthesis of two diastereomers of cytopiloyne by starting from commercially available 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-diozolane is described. The synthetic sequence involved two key steps: stereoselective glycosylation of the glucosyl trichloroacetimidate with 1-[(4-methoxybenzyl)oxy]hex-5-yn-2-ol to give the desired beta-glycoside and the construction of the glucosyl tetrayne skeleton by using a palladium/silver-catalyzed cross-coupling reaction to form the alkyne-alkyne bond, the first such use of this reaction. Comparison between the observed and published characterization data showed the 2R isomer to be the natural product cytopiloyne.
    日期: 2011-07-25
    關聯: Chemistry-A European Journal. 2011 Jul 25;17(31):8696-8703.
    Link to: http://dx.doi.org/10.1002/chem.201100986
    JIF/Ranking 2023: http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=NHRI&SrcApp=NHRI_IR&KeyISSN=0947-6539&DestApp=IC2JCR
    Cited Times(WOS): https://www.webofscience.com/wos/woscc/full-record/WOS:000294158500024
    Cited Times(Scopus): http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=79960506716
    顯示於類別:[李靜琪] 期刊論文
    [趙宇生(2002-2013)] 期刊論文

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