期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 39, 页码 13553-13557出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502113
关键词
2-deoxy sugars; antitumor antibiotic; derhodinosylurdamycin A; total synthesis; urdamycin
资金
- National Science Foundation [CHE-1213352]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1213352] Funding Source: National Science Foundation
The first total synthesis of derhodinosylurdamycin A, an angucycline antitumor antibiotic, has been described. The synthesis features a Hauser annulation followed by pinacol coupling to construct the tetracyclic angular aglycon, a Stille coupling of glycal stannane and tetracyclic aryliodide followed by stereoselective reduction to afford the 2-deoxy -C-arylglycoside, and a late-stage stereoselective glycosylation for the preparation of derhodinosylurdamycin A. This synthetic strategy should be amenable to the chemical synthesis of analogs of derhodinosylurdamycin A bearing diverse 2-deoxy sugar subunits for structure and activity relationship studies.
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