The total syntheses of C-mavacurine-type indole alkaloids, (±)-pleiocarpamine, (±)-normavacurine, and (±)- C-mavacurine, were accomplished. The key step in the syntheses was the cyclization between the metal carbenoid at C and the N position in a Corynanthe-type compound that was equipped with a diazo function. For this cyclization, the N modification of the substrate using an amine-borane complex was indispensable to fix the molecular conformation.
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