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 language | English |
|---|---|
| Pages (from-to) | 1305-1313 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2016 |
| Issue number | 7 |
| Early online date | 9 Feb 2016 |
| DOIs | |
| Publication status | Published - Mar 2016 |
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Keywords
- Copper
- Cross coupling
- Homogeneous catalysis
- Nitrogen heterocycles
- Total synthesis
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
Cite this
Mahy, W., Leitch, J. A., & Frost, C. G. (2016). Copper catalyzed assembly of N-aryloxazolidinones: synthesis of linezolid, tedizolid, and rivaroxaban. European Journal of Organic Chemistry, 2016(7), 1305-1313. https://doi.org/10.1002/ejoc.201600033