cis-Dihydrodiols, derived from monocyclic aromatic compounds, are valuable chiral pool intermediates for the synthesis of cyclic natural products. A drawback of this approach to the synthesis of polycyclic secondary metabolites, is that the additional rings must be annulated. To date, relatively few chiral natural products have been synthesized from polycyclic arene cis-dihydrodiols. Fungal metabolites ribisins A and B, have now be obtained by functional group manipulation of a major tricyclic arene metabolite, obtained from toluene dioxygenase-catalyzed regioselective and stereoselective cis-dihydroxylation of dibenzo[b,d]furan. The synthetic sequences were marginally shorter than the alternative routes using monocyclic arene cis-dihydrodiols and required no carbon-carbon bond-forming reaction.