Three synthetic approaches towards 2, 3-substituted anthracenes are reported and discussed in terms of selectivity and viability. This allowed us to introduce a variety of substituents as sidearms. Promising results have been found using a tandem Diels-Alder aromatization reaction using 2, 3-dimethoxybutadiene 9 as a key intermediate. However, for multigram preparations the Friedel-Crafts approach is preferred.