Abstract Michael reactions of 2, 5-dioxocyclohexane-1, 4-dicarboxylates with methyl vinyl ketone yield bis-adducts that can be further cyclized in a Robinson-type annulation to give s- indacene derivatives as single diastereomers. The carboxylate functions of this scaffold can be deprotected and subsequently decarboxylated to yield tricyclic products with a central aromatic ring.