Total synthesis of (-)-talaumidin and (-)-galbelgin

J Asian Nat Prod Res. 2009;11(3):281-7. doi: 10.1080/10286020802675191.

Abstract

( - )-Talaumidin (1) and ( - )-galbelgin (2) have been synthesized via 4-pentenoic acid as a starting material with the overall yield of about 17.8 and 16.9%, respectively. The key steps include Evans asymmetry anti-aldol reaction, TBS protection, hydroboration, oxidation, Friedel-Crafts arylation, etc.

MeSH terms

  • Aldehydes / chemistry
  • Fatty Acids, Monounsaturated / chemistry*
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Lignans / chemical synthesis*
  • Lignans / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aldehydes
  • Fatty Acids, Monounsaturated
  • Furans
  • Lignans
  • talaumidin
  • galgravin
  • 3-hydroxybutanal
  • 4-pentenoic acid