Stereocontrolled syntheses of epimeric 3-aryl-6-phenyl-1-oxa-7-azaspiro(4.5)decane NK-1 receptor antagonist precursors

Org Lett. 2001 Mar 8;3(5):667-70. doi: 10.1021/ol006944a.

Abstract

[structure: see text]. Complementary stereoselective syntheses of individual C3 epimers of the NK-1 receptor antagonist precursor 1 have been developed. Both diastereomers were derived from the common intermediate 3; introduction of the 3S stereocenter in 1a was achieved through hydrogenation of an arylated dihydrofuran, whereas the corresponding stereogenic center in 1b was installed using a stereo- and regioselective alkene hydroarylation.

MeSH terms

  • Aza Compounds / chemical synthesis*
  • Aza Compounds / pharmacology*
  • Chromatography, High Pressure Liquid
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Neurokinin-1 Receptor Antagonists*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / pharmacology*
  • Stereoisomerism

Substances

  • 3-aryl-6-phenyl-1-oxa-7-azaspiro(4.5)decane
  • Aza Compounds
  • Ligands
  • Neurokinin-1 Receptor Antagonists
  • Spiro Compounds