<oai_dc:dc xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:oai_dc="http://www.openarchives.org/OAI/2.0/oai_dc/" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.openarchives.org/OAI/2.0/oai_dc/ http://www.openarchives.org/OAI/2.0/oai_dc.xsd">
  <dc:creator>Kaufmann E</dc:creator>
  <dc:creator>Hattori H</dc:creator>
  <dc:creator>Miyatake-Ondozabal H</dc:creator>
  <dc:creator>Gademann K</dc:creator>
  <dc:date>2015</dc:date>
  <dc:description xmlns:ns0="xml" ns0:lang="en">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.</dc:description>
  <dc:identifier>https://sonar.ch/global/documents/109531</dc:identifier>
  <dc:language>eng</dc:language>
  <dc:relation>info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.orglett.5b01602</dc:relation>
  <dc:relation>info:eu-repo/semantics/altIdentifier/pmid/26125969</dc:relation>
  <dc:source>Organic letters. - 2015</dc:source>
  <dc:subject xmlns:ns1="xml" ns1:lang="en">Aminoglycosides</dc:subject>
  <dc:subject xmlns:ns2="xml" ns2:lang="en">Anti-Bacterial Agents</dc:subject>
  <dc:subject xmlns:ns3="xml" ns3:lang="en">Clostridium Infections</dc:subject>
  <dc:subject xmlns:ns4="xml" ns4:lang="en">Clostridium difficile</dc:subject>
  <dc:subject xmlns:ns5="xml" ns5:lang="en">Fidaxomicin</dc:subject>
  <dc:subject xmlns:ns6="xml" ns6:lang="en">Glycosylation</dc:subject>
  <dc:subject xmlns:ns7="xml" ns7:lang="en">Macrolides</dc:subject>
  <dc:subject xmlns:ns8="xml" ns8:lang="en">Molecular Structure</dc:subject>
  <dc:subject xmlns:ns9="xml" ns9:lang="en">Vancomycin</dc:subject>
  <dc:title xmlns:ns10="xml" ns10:lang="en">Total Synthesis of the Glycosylated Macrolide Antibiotic Fidaxomicin.</dc:title>
  <dc:type>http://purl.org/coar/resource_type/c_6501</dc:type>
</oai_dc:dc>
