4.8 Article

A Rapid Synthesis of 4-Oxazolidinones: Total Synthesis of Synoxazolidinones A and B**

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 21, Pages 5401-5404

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402310

Keywords

antimicrobial agents; heterocycles; natural products; stereoselectivity; total synthesis

Funding

  1. North Carolina State University
  2. NCSU Department of Chemistry

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A five-step total synthesis of the marine natural product synoxazolidinoneA was achieved through a diastereoselective imine acylation/cyclization cascade. Synoxazolidinone B and a series of analogues were also prepared to explore the potential of these 4-oxazolidinone natural products as antimicrobial agents. These studies confirmed the importance of the chlorine substituent for antimicrobial activity and revealed simplified dichloro derivatives that are equally potent against several bacterial strains.

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