Total synthesis of natural p-quinol cochinchinenone

Org Lett. 2012 Dec 7;14(23):5952-5. doi: 10.1021/ol302858r. Epub 2012 Nov 20.

Abstract

Cochinchinenone has been synthesized in only five steps and four pots and in 58% overall yield from commercially available 2,3-dimethoxy-4-hydroxy-benzaldehyde and OPMB-protected p-hydroxy acetophenone, the key step being the oxone-mediated oxidative dearomatization of the corresponding ketone-containing p-substituted phenol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Biological Products / isolation & purification
  • Biological Products / pharmacology
  • Catalysis
  • Chalcones / chemical synthesis*
  • Chalcones / chemistry
  • Chalcones / isolation & purification
  • Chalcones / pharmacology
  • Helicobacter pylori / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Anti-Bacterial Agents
  • Biological Products
  • Chalcones
  • cochinchinenone