1H-imidazole; iodine; triphenylphosphine in benzene T=20°C; Iodination; 3 h;

sodium iodide in acetone T=60 - 70°C; 6 h;

1: 90 percent / PDC / CH2Cl2 / 6 h / Ambient temperature 2: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C 3: 65 percent / CuI, Zn / ethanol; H2O / 0.67 h / sonication View Scheme

dipyridinium dichromate in dichloromethane 6 h; Ambient temperature;

1: 90 percent / PDC / CH2Cl2 / 6 h / Ambient temperature 2: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C View Scheme

1: 90 percent / PDC / CH2Cl2 / 6 h / Ambient temperature 2: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C 3: 65 percent / CuI, Zn / ethanol; H2O / 0.67 h / sonication 4: 86 percent / Et3N / (Ph3P)2PdCl2 / dimethylformamide / 1 h / 75 °C 5: 97 percent / quinoline, Lindlar catalyst, H2 / hexane / 8 h 6: 96 percent / 2,2,4-trimethyl-pentane / 5 h / Heating; in the dark 7: diethyl ether; tetrahydrofuran / 10 h / Ambient temperature 8: TBAF / tetrahydrofuran / 24 h / Ambient temperature; in the dark View Scheme

1: 75 percent / CuI, Zn / ethanol; H2O / 0.67 h / Ambient temperature; sonicated 2: 99 percent / pyridinium dichromate 3: 89 percent / n-butyllithium / -78 °C 4: 2. tetra-n-butylammonium fluoride / 1. diethyl ether, -78 deg C, 2. THF View Scheme

1: 75 percent / CuI, Zn / ethanol; H2O / 0.67 h / Ambient temperature; sonicated 2: 99 percent / pyridinium dichromate View Scheme

1: acrylic acid methyl ester With pyridine; NiII chloride hexahydrate; zinc T=20 - 60°C; 2: (1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol T=20°C; 1.5 h;

1: 90 percent / PDC / CH2Cl2 / 6 h / Ambient temperature 2: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C 3: 65 percent / CuI, Zn / ethanol; H2O / 0.67 h / sonication 4: 86 percent / Et3N / (Ph3P)2PdCl2 / dimethylformamide / 1 h / 75 °C 5: 97 percent / quinoline, Lindlar catalyst, H2 / hexane / 8 h 6: 96 percent / 2,2,4-trimethyl-pentane / 5 h / Heating; in the dark View Scheme