The spirooxindole scaffolds featuring a 3,3'-pyrrolidinyl ring are pivotal within the spirooxindole family, prevalent in natural alkaloids and bioactive compounds, offering potential for novel pharmaceutical development. Chemists recognizing the intricate molecular architecture of 3,3'-pyrrolidinyl spirooxindoles and have developed various methodologies to synthesize diverse and stereochemical controlled analogues, aiming to facilitate their evaluation for bioactivity in line with the structure-activity relationship principle in drug design. Due to their pivotal role and potential pharmacological efficacy, the 3,3'pyrrolidinyl spirooxindole scaffolds garner considerable interest among chemists in the realms of synthetic organic chemistry and medicinal chemistry. Figure displays representative natural products and pharmaceutical compounds containing a 3,3'pyrrolidinyl-spirooxindole framework. Rhynchophylline (1) exhibits significant antihypertensive, neuroprotective, and potassium ion channel activity. Furthermore, natural alkaloids spirotryprotatins A (2) and B (3) demonstrate inhibition of microtubule assembly activity, thereby attracting attention for their role in synthesizing and exploring novel antitumor agents within this compound class. Isopteropodine (4) exhibits the ability to diminish the activity of muscarinic serotonin receptors. Structurally simple alkaloids like horsifiline (5) and coerulescine (6) are well known as analgesic agent. A uniquely targeted treatment for melanoma is enabled by (+)-Elacomine (7), a natural anticancer agent found in certain shrubs of the Elaeagnus genus. MI-147(8), a small molecule based on naturally occurring spirotryprostatin A, designed rationally, functions as a specific, potent inhibitor of MDM2-p53 interaction to selectively inhibiting the growth of tumor cells. Spirooxindole compounds also exhibit a diverse array of significant biological activities, encompassing bactericidal, fungicidal, and anticancer properties, among others. Consequently, the exploration of 3,3'-pyrrolidinyl-spirooxindole derivatives particularly enticing. 12 Scheme 1. General reaction for reductive cyclization cascade and present work Significant endeavours have been devoted to enhancing the synthetic methodologies for the production of medically significant and structurally diverse 3,3'-pyrrolidinyl spirooxindoles, facilitating biological screenings. Over recent decades, numerous approaches have been developed for synthesizing 3,3'-pyrrolidinyl-spirooxindole motifs. Specifically, 1,3-dipolar reaction, Michael/cyclization reaction sequence, [3+2] cycloaddition, etc. has been documented in literature.