Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins

J Org Chem. 2005 Jul 22;70(15):6129-32. doi: 10.1021/jo050797i.

Abstract

The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph(3)PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • Acylation
  • Anti-Bacterial Agents / chemical synthesis*
  • Enzyme Inhibitors / chemical synthesis*
  • Furans / chemistry
  • Glyceric Acids / chemistry
  • Molecular Structure
  • Palmitic Acid / chemistry
  • Phosphoprotein Phosphatases / antagonists & inhibitors*
  • Phosphoprotein Phosphatases / chemical synthesis

Substances

  • Anti-Bacterial Agents
  • Enzyme Inhibitors
  • Furans
  • Glyceric Acids
  • RK 682
  • agglomerin A
  • agglomerin B
  • agglomerin C
  • Palmitic Acid
  • glyceric acid
  • Phosphoprotein Phosphatases
  • tetronic acid
  • 4-Butyrolactone