Regio- and Chemoselective Multiple Functionalization of Chloropyrazine Derivatives. Application to the Synthesis of Coelenterazine

Successive regio- and chemoselective metalations of chloropyrazines using TMPMgCl·LiCl and TMPZnCl·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 vic...

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Published inOrganic letters Vol. 11; no. 15; pp. 3406 - 3409
Main Authors Mosrin, Marc, Bresser, Tomke, Knochel, Paul
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.08.2009
Amer Chemical Soc
Subjects
Animals
Chemistry
Chemistry, Organic
Imidazoles - chemical synthesis
Imidazoles - chemistry
Organometallic Compounds - chemistry
Physical Sciences
Pyrazines - chemical synthesis
Pyrazines - chemistry
Pyruvaldehyde - chemical synthesis
Pyruvaldehyde - chemistry
Science & Technology
Scyphozoa - chemistry
CARBON BOND FORMATION
ROUTE
METALATION
CROSS-COUPLING REACTION
AROMATICS
ZINCATION
PYRAZINE
BIOLUMINESCENCE
HIGHLY EFFICIENT
CENTER-DOT-LICL
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Summary:Successive regio- and chemoselective metalations of chloropyrazines using TMPMgCl·LiCl and TMPZnCl·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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol901275n