potassium hydroxide; hydrazine hydrate in diethylene glycol 2 h; Heating;

1: AlCl3 2: H2 / Pd-C 3: polyphosphoric acid 4: (i) LiAlH4, (ii) Al2O3 View Scheme

1: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1h, RT, 2b) 30 min, reflux 2: 92 percent / NaBH4 / methanol / 10 h 3: 95 percent / lithium, liquid ammonia / diethyl ether / 1 h 4: Jones'reagent / acetone / 6 h 5: 92 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 6: 90 percent / LiBr, Li2CO3 / dimethylformamide / 0.75 h / Heating 7: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1 h, RT, 2b) 30 min, reflux View Scheme

1: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1h, RT, 2b) 30 min, reflux 2: 92 percent / NaBH4 / methanol / 10 h 3: 95 percent / lithium, liquid ammonia / diethyl ether / 1 h 4: Jones'reagent / acetone / 6 h 5: 92 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 6: 90 percent / LiBr, Li2CO3 / dimethylformamide / 0.75 h / Heating 7: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1 h, RT, 2b) 30 min, reflux 8: 90 percent / NaOH, AgNO3 / ethanol; H2O / 4 h View Scheme

1: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1h, RT, 2b) 30 min, reflux 2: 92 percent / NaBH4 / methanol / 10 h 3: 95 percent / lithium, liquid ammonia / diethyl ether / 1 h 4: Jones'reagent / acetone / 6 h View Scheme