A green stereoselective synthesis of spiroheterocycles incorporating spirooxindole and 1,2,3,4-tetrahydro-β-carboline (THβC) are demonstrated here by the one pot three-component reaction of THβC, isatins and chalcones. Operational simplicity and chromatography-free isolation are the highlights of the reaction which resulted in densely substituted spiroheterocycles with four-contiguous stereocentres in excellent yields. Activity of the compounds as anticancer agents were studied in silico against MDM2 and PLK1 target proteins and the compound shows high level of binding interactions compared to reference drugs