Application of Pd(0)-catalyzed intramolecular oxazine formation to the efficient total synthesis of (-)-anisomycin

Org Lett. 2007 Aug 30;9(18):3627-30. doi: 10.1021/ol701519b. Epub 2007 Aug 8.

Abstract

The enantioselective total synthesis of (-)-anisomycin, a potent antibiotic agent, has been achieved. The key steps are a Pd(0)-catalyzed stereoselective intramolecular oxazine formation from d-tyrosine and pyrrolidine formation by catalytic hydrogenation of the oxazine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisomycin / chemical synthesis*
  • Anisomycin / chemistry
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Catalysis
  • Molecular Structure
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry
  • Palladium / chemistry*
  • Pyrrolidines / chemistry
  • Tyrosine / chemistry

Substances

  • Anti-Bacterial Agents
  • Oxazines
  • Pyrrolidines
  • Tyrosine
  • Palladium
  • Anisomycin