Regio- and chemoselective multiple functionalization of chloropyrazine derivatives. Application to the synthesis of coelenterazine.
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.
Mosrin
Marc
M
Department Chemie & Biochemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377, München, Germany.
Bresser
Tomke
T
Knochel
Paul
P
D000818:Animals; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry*; D011765:Pyruvaldehyde / Q000138:chemical synthesis* / Q000737:chemistry; D037401:Scyphozoa / Q000737:chemistry
D007093:Imidazoles; D009942:Organometallic Compounds; D011719:Pyrazines; C530465:TMPMgCl.LiCl; C017144:coelenterazine; D011765:Pyruvaldehyde