•We developed a stereoselective spiroketalization using Pd(II)-catalyst.•The mechanism explains the stability of transition state.•The reaction proceeds without activation of the allylic alcohol.We report a highly stereoselective palladium(II)-catalyzed intramolecular cyclization of 1,11-dihydroxyundec-9-en-5-one derivatives via unstable hemiacetal intermediates, in which cyclization occurs without activation of the allylic alcohol to afford spiroketal structures.