Asymmetric synthesis of a prostaglandin D2 receptor antagonist

J Org Chem. 2005 Jan 7;70(1):268-74. doi: 10.1021/jo048305+.

Abstract

An asymmetric synthesis was developed for the production of a prostaglandin D(2) receptor antagonist for the treatment of allergic rhinitis. The stereogenic center was set using asymmetric allylic alkylation chemistry, and the core of the structure was constructed via Pd-catalyzed N-cyclization/Heck methodology. The synthesis relies on a late stage indoline oxidation which does not racemize the product.

MeSH terms

  • Combinatorial Chemistry Techniques*
  • Crystallography, X-Ray
  • Cyclization
  • Indoles / chemical synthesis*
  • Indoles / pharmacology
  • Molecular Conformation
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / pharmacology
  • Oxidation-Reduction
  • Palladium / chemistry*
  • Receptors, Immunologic / antagonists & inhibitors*
  • Receptors, Prostaglandin / antagonists & inhibitors*
  • Rhinitis, Allergic, Perennial / drug therapy*

Substances

  • Indoles
  • Organometallic Compounds
  • Receptors, Immunologic
  • Receptors, Prostaglandin
  • Palladium
  • prostaglandin D2 receptor