The pre-organized concave surfaces (active-sites) and inbuilt functionalities of enzymes are responsible for the specific recognition and transformation of substrates.  Chemists strive to mimic the elegance of enzyme catalysis by incorporating the above two qualities into synthetic analogues.  The pre-organized concavity of the deep-cavity cavitand 1a^1-2 prompted us to seek ways to functionalize the rim and inner wall as a means to create hosts with enzyme-like properties.  For example, we recently reported a range of formylated hosts from 1a using directed ortho metallation (DOM).³ We will report on our further investigations into DOM approaches to functionalization.  In addition, we will outline our investigations into simple electrophilic substitutions upon 1a, and alternative hosts 1b-d.