Following precedent by Li, Nicolaou and co-workers, 31 a 6p electrocyclization/aromatization sequence could be effected to generate arene 27. In agreement with their work, the use of CuOTf as a Lewis acid promoter was found to improve the yield of the reaction (73% isolated yield) while also effecting a concomitant hydrolysis of the TMS ether at C3. While oxidation of the C3 alcohol to the corresponding ketone proceeded uneventfully, attempts to effect a Fleming-Tamao oxidation to convert 27 to the corresponding phenol were met with failure. Similar outcomes were obtained when alternative silanes at C4' were tested in the reaction. Earlier iterations of the route featuring a late-stage sp 2 C-H oxidation at C4' using Ru catalysis or peroxide-based reagents also failed to deliver the desired product. As a workaround, silane 27 was first subjected to desilylative iodination with NIS to provide 28. Following screening of several reported conditions for haloarene hydroxylation, access to chrodrimanin C (3) could be realized through the use of Cu(acac)2 and N,N'-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) on 28. This method, initially reported by Ma and co-workers, proved superior to Pd-based hydroxylation methods and with slight modifications to the originally reported conditions, the desired phenol product could be obtained in 83% isolated yield. A-ring desaturation of 3 proceeded uneventfully under standard Saegusa conditions to deliver verruculide A (29) in 82% yield. Interestingly, TMS ether formation at the phenolic OH was not observed in this reaction, likely due to the presence of an intramolecular hydrogen bonding with the neighboring lactone. Overall, this sequence provided a 16-step synthesis of chrodrimanin C (3) and a 18-step synthesis of verruculide A (29) from sclareolide (7), respectively. As noted earlier, the biosynthetic pathway towards the chrodrimanins was recently elucidated by Matsuda, Abe and co-workers and we anticipate that future work involving incorporation of some of the enzymes from the pathway would allow for a rapid chemoenzymatic diversification of the scaffold to provide a wider range of synthetic chrodrimanins.