Pictet−Spengler Based Synthesis of a Bisarylmaleimide Glycogen Synthase Kinase-3 Inhibitor

A practical synthesis of the glycogen synthase kinase-3 (GSK3) inhibitor bisarylmaleimide 1 has been accomplished employing Pictet−Spengler methodology to access the indole 7-position in preparing the benzodiazepine tricyclic fragment. A seven-step linear sequence that starts with commercially avail...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 16; pp. 3700 - 3703
Main Authors Magnus, Nicholas A, Ley, Christopher P, Pollock, Patrick M, Wepsiec, James P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.08.2010
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Glycogen Synthase Kinase 3 - antagonists & inhibitors
Indoles - chemistry
Maleimides - chemical synthesis
Maleimides - chemistry
Maleimides - pharmacology
Molecular Structure
Physical Sciences
Science & Technology
AGENT
NITROARENES
GSK3
INDOLES
VINYL GRIGNARD-REAGENTS
TRIFLUOROACETIC-ACID
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Summary:A practical synthesis of the glycogen synthase kinase-3 (GSK3) inhibitor bisarylmaleimide 1 has been accomplished employing Pictet−Spengler methodology to access the indole 7-position in preparing the benzodiazepine tricyclic fragment. A seven-step linear sequence that starts with commercially available 5-fluoroindole 7 affords the bisarylmaleimide 1 in 33% overall yield.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol101405g