Owing to their challenging structures and promising biological profiles, spirooxindole alkaloids have long attracted much attention from the synthetic community. Herein, we wish to describe a concise, protecting-group-free total synthesis of cabucine oxindole A, a putative natural spirooxindole alkaloid and a possible biosynthetic congener of cabucine and palmirine. Key transformations of our approach include a one-step, organocatalytic and enantioselective construction of the spiro[pyrrolidine-3,3’-oxindole] moiety and a Korte rearrangement to furnish the final dihydropyran motif. Biological investigation of 1 and its synthetic intermediates revealed lactone 2 as a mild MOLT-4 and MCF7 cell line inhibitor. © 2021 SIOC, CAS, Shanghai and Wiley-VCH GmbH