1: 82 percent / pyridinium chlorochromate / Celite / CH2Cl2 / 1.5 h 2: 87 percent / diethyl ether / 16 h / Ambient temperature 3: 1.) p-toluene-sulfonic acid, 2.) NaI / 1.) THF, RT, 1 h, 2.) RT, 24 h, acetone 4: 39 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 degC, 30 min and RT, 4 h 5: 1.) O2, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH2Cl2, 30 min, irradiation, 2.) benzene, 24 h, reflux View Scheme

1: 96 percent / borane, HCl / tetrahydrofuran; methanol / 2 h 2: 82 percent / pyridinium chlorochromate / Celite / CH2Cl2 / 1.5 h 3: 87 percent / diethyl ether / 16 h / Ambient temperature 4: 1.) p-toluene-sulfonic acid, 2.) NaI / 1.) THF, RT, 1 h, 2.) RT, 24 h, acetone 5: 39 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 degC, 30 min and RT, 4 h 6: 1.) O2, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH2Cl2, 30 min, irradiation, 2.) benzene, 24 h, reflux View Scheme

1: 1.) p-toluene-sulfonic acid, 2.) NaI / 1.) THF, RT, 1 h, 2.) RT, 24 h, acetone 2: 39 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 degC, 30 min and RT, 4 h 3: 1.) O2, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH2Cl2, 30 min, irradiation, 2.) benzene, 24 h, reflux View Scheme

1: 87 percent / diethyl ether / 16 h / Ambient temperature 2: 1.) p-toluene-sulfonic acid, 2.) NaI / 1.) THF, RT, 1 h, 2.) RT, 24 h, acetone 3: 39 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 degC, 30 min and RT, 4 h 4: 1.) O2, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH2Cl2, 30 min, irradiation, 2.) benzene, 24 h, reflux View Scheme

oxygen; toluene-4-sulfonic acid; Sensitox 1.) CH2Cl2, 30 min, irradiation, 2.) benzene, 24 h, reflux; Yield given. Multistep reaction;

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