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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Kumar, Chidambaram Ramesh Chao, Yu-sheng Lee, Jinq-chyi Tsai, Chi-hui |
| Description | Author Affiliation: Kumar CR ( Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, 35, Keyan Road, Zhunan Town, Miaoli County 35053, Taiwan, ROC.) |
| Abstract | 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-β-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 β-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. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 31 |
| Volume Number | 17 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2011-07-25 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Glucosides Chemical Synthesis Hypoglycemic Agents Polyacetylenes Bidens Chemistry Catalysis Pharmacology Glycosylation Molecular Structure Stereoisomerism Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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