1: 90 percent / O2, 5,10,15,20-tetraphenyl-21H,23H-porphine, Ac2O, DMAP, pyridine / CH2Cl2 / 20 °C / Irradiation 2: 98 percent / boron trifluoride etherate / CH2Cl2 / -10 °C 3: 91 percent / lithium iodide monohydrate / various solvent(s) / Heating 4: p-toluenesulfonic acid / benzene / Heating 5: 1) p-toluenesulfonic acid, 2) aq. NaOH / 1) aq. acetone, reflux, 2) MeOH, reflux 6: 94 percent / potassium hydride, DMSO / benzene / 20 °C 7: 1) p-toluenesulfonic acid, 2) sodium hydroxide / 1) acetone, water, reflux, 2) methanol, water, 25 deg C 8: lithium aluminum hydride / tetrahydrofuran / Heating 9: Et3N / CH2Cl2 / 0 °C 10: 92 percent / lithium aluminum hydride / tetrahydrofuran / Heating 11: 89 percent / HgCl2 / acetonitrile; H2O / 20 °C 12: 100 percent / sodium borohydride, cerium(III) chloride / methanol / -78 °C 13: 92 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 20 °C 14: 1) 9-borabicyclo<3.3.1>nonane, 2) H2CrO4 / 1) THF, 20 deg C, 2) ether, 0 -> 20 deg C 15: K2CO3 / acetone / 20 °C View Scheme