Efforts towards the identification of simpler platensimycin analogues--the total synthesis of oxazinidinyl platensimycin

Chemistry. 2009;15(12):2747-50. doi: 10.1002/chem.200802568.


Epimerization and stapling in one pot: A facile synthesis of an oxazinidinyl analogue of the antibiotic platensimycin is presented. Key steps of this work are a novel dynamic ring-closing metathesis (RCM) that involves a base-catalyzed epimerization followed by a tandem Ru-catalyzed metathesis, and a nucleophilic addition to a ketone followed by a subsequent intramolecular epoxide ring-opening reaction to construct the core structure of the target molecule (see scheme).

MeSH terms

  • Adamantane / chemical synthesis*
  • Adamantane / chemistry
  • Aminobenzoates / chemical synthesis*
  • Aminobenzoates / chemistry
  • Anilides / chemical synthesis*
  • Anilides / chemistry
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Catalysis
  • Cyclization
  • Molecular Structure


  • Aminobenzoates
  • Anilides
  • Anti-Bacterial Agents
  • Adamantane
  • platensimycin