2. Academic Validation
  3. Regio- and chemoselective multiple functionalization of chloropyrazine derivatives. Application to the synthesis of coelenterazine

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.
Marc Mosrin 1,  Tomke Bresser,  Paul Knochel
Affiliations

Affiliation

  • 1 Department Chemie & Biochemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377, München, Germany.
PMID: 19719188 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.

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