Regio- and chemoselective multiple functionalization of chloropyrazine derivatives. Application to the synthesis of coelenterazine

Org Lett. 2009 Aug 6;11(15):3406-9. doi: 10.1021/ol901275n.

Abstract

Successive regio- and chemoselective metalations of chloropyrazines using TMPMgCl x LiCl and TMPZnCl x LiCl furnish, after trapping with electrophiles, highly functionalized pyrazines in high yields. Application to a synthesis of coelenterazine, a bioluminescent natural product in jellyfish Aequorea victoria, in nine steps (9% overall yield) is reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Organometallic Compounds / chemistry*
  • Pyrazines / chemical synthesis
  • Pyrazines / chemistry*
  • Pyruvaldehyde / chemical synthesis*
  • Pyruvaldehyde / chemistry
  • Scyphozoa / chemistry

Substances

  • Imidazoles
  • Organometallic Compounds
  • Pyrazines
  • TMPMgCl.LiCl
  • coelenterazine
  • Pyruvaldehyde