Copper catalyzed assembly of N-aryloxazolidinones: synthesis of linezolid, tedizolid, and rivaroxaban

William Mahy, Jamie A. Leitch, Christopher G. Frost

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The total synthesis of oxazolidinone-based pharmaceuticals, linezolid, tedizolid and rivaroxaban is reported. They are synthesized using a recently reported copper-catalyzed one-pot cyclization and arylation as the key step to construct the N-aryloxazolidinone core. Active pharmaceutical ingredients (API) were synthesized from a common synthetic pool of a simple protected amino alcohol in 22%, 61% and 40% total synthesis yields, respectively.

Original languageEnglish
Pages (from-to)1305-1313
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number7
Early online date9 Feb 2016
DOIs
Publication statusPublished - Mar 2016

Keywords

  • Copper
  • Cross coupling
  • Homogeneous catalysis
  • Nitrogen heterocycles
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Fingerprint Dive into the research topics of 'Copper catalyzed assembly of <i>N</i>-aryloxazolidinones: synthesis of linezolid, tedizolid, and rivaroxaban'. Together they form a unique fingerprint.

Cite this