Here we report the total synthesis of clovan-2,9-dione via Rhcatalyzed [3 + 2 + 1] cycloaddition/hydroformylation/aldol reaction. The [3 + 2 + 1] reaction of 1-yne-vinylcyclopropane and CO was used for the generation of a 5/6 bicyclic skeleton with a bridgehead vinyl group. The hydroformylation reaction converted the congested olefin of the [3 + 2 + 1] cycloadduct to a one-carbon elongated aldehyde, which underwent in situ aldol reaction, with the carbonyl group in the [3 + 2 + 1] cycloadduct, to generate the tricyclic bridged-ring skeleton of the target molecule.