Organic Letters 2010-08-20

Pictet-Spengler based synthesis of a bisarylmaleimide glycogen synthase kinase-3 inhibitor.

Nicholas A Magnus, Christopher P Ley, Patrick M Pollock, James P Wepsiec

Index: Org. Lett. 12 , 3700-3703, (2010)

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Abstract

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.