thionyl chloride in diethyl ether 16 h; Ambient temperature;

dicyclohexyl-carbodiimide in acetone T=46°C; 3 h;

1: 1.) O3, 2.) H2O2 / 1.) CH2Cl2, CH3COOH, -78 deg C, 2.) CH3COOH 2: (CH3CO)2O / 14 h / Ambient temperature View Scheme

22 h; Mechanism;

1: pyridine / diethyl ether / 10 h / Ambient temperature 2: 2.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) chloroform, RT, 12 h, 2.) chloroform, 8 h, reflux, 12 h 3: 100 percent / hydrogen / platinum oxide / acetic acid / 24 h 4: 74 percent / 1M-barium hydroxide / H2O / 1 h / Heating View Scheme

1: pyridine / diethyl ether / 10 h / Ambient temperature 2: 2.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) chloroform, RT, 12 h, 2.) chloroform, 8 h, reflux, 12 h 3: 100 percent / hydrogen / platinum oxide / acetic acid / 24 h 4: 76 percent / liquid ammonia, sodium / methanol View Scheme

methanol; lithium borohydride; quinine powder 1.) Et2O, r.t., 1 d; Yield given. Multistep reaction. Title compound not separated from byproducts;

sodium tetrahydroborate in isopropyl alcohol

1: pyridine / diethyl ether / 10 h / Ambient temperature 2: 2.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) chloroform, RT, 12 h, 2.) chloroform, 8 h, reflux, 12 h 3: 57 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 96 h / Ambient temperature 4: hydrogen / platinum oxide / acetic acid 5: 1.) 1M-diborane, 2.) barium hydroxide / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 1 h, 3.) water, RT, 12 h View Scheme

methanol; lithium borohydride; quinine powder 1.) Et2O, r.t., 1 d; Yield given. Multistep reaction. Title compound not separated from byproducts;