The cytotoxic furan derivative (+/-)-4-ipomeanol (1) and its regioisomer (8) were prepared in a new and efficient way starting from commercially available furan derivatives. In both cases the key step was a regioselective solvolysis of the terminal double bond with trifluoroacetic anhydride and boron trifluoride. The resulting compounds were tested in an agar diffusion assay against several bacteria and fungi, but did not show significant activity.