Ring contraction reaction is among the several vital strategies in organic synthesis that can provide very diversified and useful molecular architecture. Among these strategies, the oxida-tive ring contraction is of special interest as it can give a more straightforward way of designing and synthesizing several complex natural products, specifically the oxindole alkaloids and some newer oxindole analogs. Even this methodology can be expanded to prepare dispiro-bisoxindoles-type compounds besides the dipolar cycloaddition methodology. In this review, we have tried to collect the reports on oxidative ring contraction reactions using several oxidants, like tert-Butyl hypo-chlorite, oxaziridine, dimethyldioxirane, N-bromosuccinimide, etc., in different reaction conditions for the synthesis of spiro-oxindole natural products as well as newer synthetic analogs. © 2023 Bentham Science Publishers.