Synthetic studies towards the novel fomannosane sesquiterpenoid illudosin: framework construction

A synthetic approach to the novel fomannosane sesquiterpene natural product illudosin from the diquinane precursor , readily available in turn from commercial 1,5-cyclooctadiene, is delineated. The key steps are the stereoselective construction of the cis, anti, cis-tricyclo[6.2.0.02,6]decane system, strategic C–C bond disengagement through Baeyer–Villiger oxidation and functional group adjustments to deliver the carbocyclic core present in the natural product.