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Asymmetric catalysis has continued to enable the preparation of optically active natural products over the past decade. This minireview summarizes progress in the catalytic enantioselective total synthesis of complex monoterpenoid indole alkaloids covering the reports from 2019 to June 2021. In particular, generation of the key chiral stereogenic centers with metal catalysts and organocatalysts has been highlighted, showcasing the power of asymmetric catalysis protocols in accessing complex molecular architectures.