Stereoselective Synthesis of a Dipyridyl Transient Receptor Potential Vanilloid-3 (TRPV3) Antagonist

J Org Chem. 2016 Dec 2;81(23):12060-12064. doi: 10.1021/acs.joc.6b02443. Epub 2016 Nov 14.

Abstract

An efficient asymmetric synthesis of dipyridyl TRPV3 antagonist 1 is reported. The four-step route involves two C-C bond-forming steps, a highly diastereoselective alkene hydration, and asymmetric ketone hydrosilylation in 97% ee.

MeSH terms

  • Carbon-13 Magnetic Resonance Spectroscopy
  • Humans
  • Proton Magnetic Resonance Spectroscopy
  • Pyridines / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism
  • TRPV Cation Channels / antagonists & inhibitors*

Substances

  • Pyridines
  • TRPV Cation Channels
  • TRPV3 protein, human