Total synthesis of wedelolactone

J Org Chem. 2003 Oct 31;68(22):8500-4. doi: 10.1021/jo030228f.

Abstract

The total synthesis of wedelolactone, a naturally occurring direct inhibitor of IKK complex that can suppress LPS-induced caspase-11 expression, using a convergent synthetic approach, is described. The key steps involved in this synthesis include the palladium-catalyzed Sonogashira reaction and the palladium-catalyzed carbonylative annulation reaction. This approach allows access to diversified analogues of wedelolactone.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carrier Proteins / antagonists & inhibitors
  • Carrier Proteins / chemistry
  • Caspase Inhibitors
  • Caspases / chemistry
  • Coumarins / chemical synthesis*
  • Coumarins / pharmacology
  • Intracellular Signaling Peptides and Proteins
  • Lipopolysaccharides / antagonists & inhibitors
  • Magnetic Resonance Spectroscopy
  • Palladium / chemistry
  • Structure-Activity Relationship

Substances

  • Carrier Proteins
  • Caspase Inhibitors
  • Coumarins
  • Ikbkap protein, mouse
  • Intracellular Signaling Peptides and Proteins
  • Lipopolysaccharides
  • wedelolactone
  • Palladium
  • Caspases