titanium tetrachloride; magnesium; mercury dichloride in tetrahydrofuran 1.) 0 deg C, 2 h, 2.) reflux, 24 h;

1: 83 percent / dimethylformamide / 48 h / 150 °C 2: 89 percent / KOH / ethanol; H2O / 72 h / Heating 3: diethyl ether 4: Irradiation View Scheme

1: 96 percent / PCC; Celite / CH2Cl2 / 20 °C 2: 83 percent / dimethylformamide / 48 h / 150 °C 3: 89 percent / KOH / ethanol; H2O / 72 h / Heating 4: diethyl ether 5: Irradiation View Scheme

1: 89 percent / KOH / ethanol; H2O / 72 h / Heating 2: diethyl ether 3: Irradiation View Scheme

1.1: iPr2NH; nBuLi; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 2 h / -78 °C 1.2: tetrahydrofuran 2.1: LiAlH4 / tetrahydrofuran / Heating 3.1: PCC; Celite / CH2Cl2 4.1: tetrahydrofuran / 2 h / 0 °C 5.1: 96 percent / PCC; Celite / CH2Cl2 / 20 °C 6.1: 83 percent / dimethylformamide / 48 h / 150 °C 7.1: 89 percent / KOH / ethanol; H2O / 72 h / Heating 8.1: diethyl ether 9.1: Irradiation View Scheme

1: PCC; Celite / CH2Cl2 2: tetrahydrofuran / 2 h / 0 °C 3: 96 percent / PCC; Celite / CH2Cl2 / 20 °C 4: 83 percent / dimethylformamide / 48 h / 150 °C 5: 89 percent / KOH / ethanol; H2O / 72 h / Heating 6: diethyl ether 7: Irradiation View Scheme

1: diethyl ether 2: Irradiation View Scheme

1: diethyl ether 2: I2 / 150 °C View Scheme

iodine T=150°C;

toluene-4-sulfonic acid 2.)reflux; Multistep reaction;