A simple and reliable approach was developed for the stereoselective construction of symmetrical linear dioxatriquinanes and oxadiquinanes via Lewis acid mediated nucleophilic addition to oxonium ion intermediate for etherification of dimethyl acetals. The precursors of linear triquinanes are obtained from the Diels-Alder adducts via ozonolysis in MeOH followed by reductive work-up and subsequent treatment with catalytic H2SO4 to furnish the dimethyl acetal. Further, the stereochemistry of synthesized oxa-bowls was unambiguously established by single crystal X-ray diffraction studies on its derivative.