A novel route to the vinyl sulfide nine-membered macrocycle moiety of Griseoviridin

J Org Chem. 2000 Jul 28;65(15):4553-9. doi: 10.1021/jo000116d.

Abstract

The synthetic potentialities of cerium(III) chloride are demonstrated by the synthesis of a nine-membered ring heterocycle component of Griseoviridin (3) in optically active form. The key step involves the stereospecific formation of the alpha-carbalkoxy alkenyl sulfide moiety using a combination system of cerium(III) chloride heptahydrate and sodium iodide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Cerium / chemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Magnetic Resonance Spectroscopy
  • Peptides*
  • Sodium Iodide / chemistry
  • Stereoisomerism
  • Streptomyces / chemistry*
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry
  • Virginiamycin / chemical synthesis*
  • Virginiamycin / chemistry

Substances

  • Anti-Bacterial Agents
  • Heterocyclic Compounds
  • Peptides
  • Sulfides
  • Virginiamycin
  • Cerium
  • griseoviridin
  • Sodium Iodide
  • cerous chloride