title: Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A.
abstract: 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 β-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.
authors.affiliation: Department of Chemistry and Biochemistry.
authors.forename: Hem Raj
authors.initials: HR
authors.lastname: Khatri
authors.affiliation: Department of Chemistry and Biochemistry.
authors.forename: Hai
authors.initials: H
authors.lastname: Nguyen
authors.affiliation: Department of Chemistry and Biochemistry.
authors.forename: James K
authors.initials: JK
authors.lastname: Dunaway
authors.affiliation: Department of Chemistry and Biochemistry. Jianglong.Zhu@utoledo.edu.|School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606 (USA), Fax: (+1) 419-530-4033. Jianglong.Zhu@utoledo.edu.
authors.forename: Jianglong
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry*; D003837:Deoxy Sugars / Q000737:chemistry*; D006031:Glycosylation; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D003837:Deoxy Sugars; D006146:Guanidines; D009844:Oligosaccharides; C000607397:derhodinosylurdamycin A
keywords: 2-deoxy sugars; antitumor antibiotic; derhodinosylurdamycin A; total synthesis; urdamycin