A Divergent Route to Eravacycline

J Org Chem. 2017 Jan 20;82(2):936-943. doi: 10.1021/acs.joc.6b02442. Epub 2017 Jan 6.

Abstract

A convergent route to eravacycline (1) has been developed by employing Michael-Dieckmann cyclization between enone 3 and a fully built and protected left-hand piece (LHP, 2). After construction of the core eravacycline structure, a deprotection reaction was developed, allowing for the isoxazole ring opening and global deprotection to be achieved in one pot. The LHP is synthesized from readily available 4-fluoro-3-methylphenol in six steps featuring a palladium-catalyzed phenyl carboxylation in the last step.

MeSH terms

  • Cresols / chemistry
  • Cyclization
  • Molecular Structure
  • Tetracyclines / chemical synthesis*
  • Tetracyclines / chemistry

Substances

  • Cresols
  • Tetracyclines
  • eravacycline
  • cresol