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This <jats:italic>C<\/jats:italic><jats:sub>3<\/jats:sub> symmetric compound has three bicyclo[3.1.1]heptane rings fused to its central benzene with each ring carrying a carbonyl group. The cyclotrimer undergoes diastereoselective threefold alkynylation with the lithium salts of five terminal alkynes (41\u201363\u2009%, <jats:italic>de<\/jats:italic>=4\u201383\u2009%). The addition enabled a rapid synthesis of a small library of novel chiral cavitands that, in shape, resemble a tripod stand. These molecular tripods include a tris\u2010bicycloannelated benzene head attached to three alkyne legs twisted in one direction to form a nonpolar cavity with polar groups as feet. Tripods with methylpyridinium and methylisoquinolinium legs, respectively, form inclusion complexes with anti\u2010inflammatory and chiral drugs (<jats:italic>R<\/jats:italic>)\/(<jats:italic>S<\/jats:italic>)\u2010ibuprofen and (<jats:italic>R<\/jats:italic>)\/(<jats:italic>S<\/jats:italic>)\u2010naproxen. The mode of binding shows drug molecules docked in the cavity of the host through ion\u2010ion, cation\u2010\u03c0, and C\u2212H\u2212\u03c0 contacts that, in addition of desolvation, give rise to complexes having millimolar to micromolar stability in water. 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