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Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A
Author(s) -
Khatri Hem Raj,
Nguyen Hai,
Dunaway James K.,
Zhu Jianglong
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502113
Subject(s) - glycal , stereoselectivity , stannane , chemistry , stereochemistry , annulation , total synthesis , stille reaction , glycosylation , pinacol , formal synthesis , aglycone , combinatorial chemistry , organic chemistry , glycoside , biochemistry , catalysis
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.