Abstract
A concise and efficient synthesis of 1-deaza-eupolauramine 2 is disclosed. The key steps are the connection of a metalated isoindolinone equipped with the synthetic auxiliary benzotriazolyl group with an ortho-halogenobenzaldehyde, followed by interception of the transient oxanion with bulky pivaloyl chloride. Removal of the temporary auxiliary under acidic conditions followed by free radical cyclization of the resulting enelactam derivative and ultimate replacement of the pivaloyloxy group by the methoxy functionality completes the synthesis of the targeted compound.
Cuvinte cheie
isoindolinones
benzotriazole
metalation
oxidative cyclization
alkaloids
eupolauramine