Conventional retrosynthetic analysis in electrophilic aromatic substitution (EAS) reactions has a different “flavor” than in alkyne reactions. There are a variety of functional groups, with corresponding directing effects, leading to many more interesting possibilities. Even when the number of functional groups on the aromatic ring is limited, the syntheses can still present challenge. Take, for example, the synthesis of tetrahydro-indacene-dione (dubbed by a friend as “mad beetle dione”) 2 starting with bromohexynyl-arene 1 (Scheme 1).
