Synthetic Study towards Strictamine: The Oxidative Coupling Approach

A synthetic approach featuring a key intramolecular oxidative coupling of a dianion for the formation of the C7-C16 bond was exploited aiming at the synthesis of strictamine. Treatment of substituted tetrahydrocarboline with LHMDS at -78 degrees C followed by iodine at room temperature afforded a tetracyclic compound, a substructure of eburnane-type alkaloid, via the formation of the N-a-C16 bond.