Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A |
| |
Authors: | Hem Raj Khatri Hai Nguyen James K. Dunaway Prof. Dr. Jianglong Zhu |
| |
Affiliation: | 1. Department of Chemistry and Biochemistry;2. School of Green Chemistry and Engineering, The University of Toledo, 2801?W. Bancroft Street, Toledo, OH 43606 (USA), Fax: (+1)?419‐530‐4033 |
| |
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. |
| |
Keywords: | 2‐deoxy sugars antitumor antibiotic derhodinosylurdamycin A total synthesis urdamycin |
|
|