Synthesis and Antibacterial Activity of Four Stereoisomers of the Spider-Pathogenic Fungus Metabolite Torrubiellone D

Org Lett. 2016 Mar 4;18(5):1136-9. doi: 10.1021/acs.orglett.6b00245. Epub 2016 Feb 12.

Abstract

Four stereoisomers of the spider-pathogenic fungus metabolite torrubiellone D were synthesized for the first time in 10% overall yield starting from L-tyrosine or D-tyrosine. The 3-decatrienoyl side chain was assembled and attached via (E)-selective HWE and Wittig olefinations. Their antibiotic activities against drug-susceptible Escherichia coli strains differed considerably.

MeSH terms

  • Alkaloids* / chemical synthesis
  • Alkaloids* / chemistry
  • Alkaloids* / isolation & purification
  • Alkaloids* / pharmacology
  • Animals
  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / isolation & purification
  • Anti-Bacterial Agents* / pharmacology
  • Enterococcus faecium / drug effects
  • Escherichia coli / drug effects
  • Hypocreales / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyrrolidinones / chemistry
  • Spiders / microbiology*
  • Staphylococcus aureus / drug effects
  • Stereoisomerism
  • Tyrosine / chemistry

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Pyrrolidinones
  • torrubiellone D
  • Tyrosine
  • tetramic acid