Due to their strong antiproliferative activity and their unprecedented structural complexity within the class of indole alkaloids, avrainvillamide and stephacidin B have recently attracted considerable interest from the synthetic community. To date, three distinct approaches towards these molecules have been disclosed and the present tutorial review aims at comparing all three syntheses with a focus on the various strategies and methods employed. Besides, recent progress towards the synthesis of structural analogs and the identification of the biological target of avrainvillamide will be presented.