In summary, the synthesis of a macrocycle 1 was revisited. We further showed that the use of 1 as a precursor is crucial towards the successful formation of a wide range of pillar [4]naphthalene derivatives (2) and a pillar [4]anthracene (3). Since the transformations begin with a structurally precise cyclic tetramer precursor, historic issues encountered in macrocycle formation, such as the need of high-dilution reaction medium and/or the need of a templating guest during reaction, unwanted polymerization, and non-selective macrocycle formation, are thus avoided. Exploration of selective access to other members of calix[n]furan and subsequent conversion to their corresponding pillar[n]arene-type macrocycles, as well as their host-guest properties are currently going on in our laboratory, and the result will be reported in due course.