1: 77 percent / S. cerevisiae; dextrose; H2O / CaCO3; MgSO4 / 18 h / 35 °C 2: DBU / dimethylsulfoxide / 1 h / 20 °C 3: 22 g / DBU / dimethylsulfoxide / 12 h / 20 °C 4: 90 percent / 3.5 h / 190 °C 5: 82 percent / LiAlH4 / diethyl ether / 0 - 20 °C 6: 92 percent / imidazole / dimethylformamide / 24 h / 20 °C 7: O3; NaOH / methanol; CH2Cl2 / -78 °C 8: 0.98 g / methanol / 0 - 20 °C 9: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C View Scheme

5,15,10,20-tetraphenylporphyrin in dichloromethane Ambient temperatureIrradiation;

1: O3; NaOH / methanol; CH2Cl2 / -78 °C 2: 0.98 g / methanol / 0 - 20 °C 3: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C View Scheme

1: DBU / dimethylsulfoxide / 1 h / 20 °C 2: 22 g / DBU / dimethylsulfoxide / 12 h / 20 °C 3: 90 percent / 3.5 h / 190 °C 4: 82 percent / LiAlH4 / diethyl ether / 0 - 20 °C 5: 92 percent / imidazole / dimethylformamide / 24 h / 20 °C 6: O3; NaOH / methanol; CH2Cl2 / -78 °C 7: 0.98 g / methanol / 0 - 20 °C 8: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C View Scheme

1: 90 percent / 3.5 h / 190 °C 2: 82 percent / LiAlH4 / diethyl ether / 0 - 20 °C 3: 92 percent / imidazole / dimethylformamide / 24 h / 20 °C 4: O3; NaOH / methanol; CH2Cl2 / -78 °C 5: 0.98 g / methanol / 0 - 20 °C 6: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C View Scheme

1: K2CO3 / acetone / 2 h / Heating 2: 41 percent Spectr. / tetraphenylporphine / CH2Cl2 / Ambient temperature; Irradiation View Scheme

oxygen; rose bengal T=-20°C; 2.5 h; Irradiation; Title compound not separated from byproducts;

oxygen; rose bengal T=-20°C; 2.5 h; Irradiationother solvents, other temperature; Product distribution;

oxygen; rose bengal T=-35°C; 3 h; Irradiation; Product distribution;