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Total Synthesis of the Glycosylated Macrolide Antibiotic Fidaxomicin.
Journal article

Total Synthesis of the Glycosylated Macrolide Antibiotic Fidaxomicin.

  • Kaufmann E Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
  • Hattori H Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
  • Miyatake-Ondozabal H Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
  • Gademann K Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
  • 2015-07-01
Published in:
  • Organic letters. - 2015
Aminoglycosides
Anti-Bacterial Agents
Clostridium Infections
Clostridium difficile
Fidaxomicin
Glycosylation
Macrolides
Molecular Structure
Vancomycin
English The first enantioselective total synthesis of fidaxomicin, also known as tiacumicin B or lipiarmycin A3, is reported. This novel glycosylated macrolide antibiotic is used in the clinic for the treatment of Clostridium difficile infections. Key features of the synthesis involve a rapid and high-yielding access to the noviose, rhamnose, and orsellinic acid precursors; the first example of a β-selective noviosylation; an effective Suzuki coupling of highly functionalized substrates; and a ring-closing metathesis reaction of a noviosylated dienoate precursor. Careful selection of protecting groups allowed for a complete deprotection yielding totally synthetic fidaxomicin.
Language
  • English
Open access status
hybrid
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Persistent URL
https://sonar.ch/global/documents/109531
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