Total synthesis and absolute configuration of laurenditerpenol: a hypoxia inducible factor-1 activation inhibitor

J Med Chem. 2007 Dec 13;50(25):6299-302. doi: 10.1021/jm7011062. Epub 2007 Nov 16.

Abstract

The absolute stereo structure of the natural product laurenditerpenol (1S, 6R, 7S, 10R, 11R, 14S, 15R) has been accomplished from eight plausible stereoisomers by its first asymmetric total synthesis in a highly convergent and flexible synthetic pathway. Six stereoisomers of laurenditerpenol were synthesized and evaluated for their biological activity.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cell Hypoxia
  • Cell Line, Tumor
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology
  • Humans
  • Hypoxia-Inducible Factor 1 / antagonists & inhibitors*
  • Hypoxia-Inducible Factor 1 / biosynthesis
  • Molecular Conformation
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Diterpenes
  • Hypoxia-Inducible Factor 1
  • laurenditerpenol