A symmetry-based concise formal synthesis of platencin, a novel lead against "superbugs"

Angew Chem Int Ed Engl. 2009;48(29):5372-5. doi: 10.1002/anie.200902338.

Abstract

Quick access: A concise and efficient formal synthesis of platencin has been accomplished in nine steps from a commercially available starting material. The synthesis utilized only one protecting group. The base-catalyzed Michael cyclization of precursor 1 afforded the key diketone 2, which was converted into the desired core structure 4 via the radical intermediate 3.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminophenols / chemical synthesis*
  • Anti-Bacterial Agents / chemical synthesis*
  • Cyclization
  • Ketones / chemistry
  • Polycyclic Compounds / chemical synthesis*
  • Stereoisomerism
  • Streptomyces / chemistry*

Substances

  • Aminophenols
  • Anti-Bacterial Agents
  • Ketones
  • Polycyclic Compounds
  • platencin