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: 92 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 2: 90 percent / LiBr, Li2CO3 / dimethylformamide / 0.75 h / Heating 3: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1 h, RT, 2b) 30 min, reflux View Scheme

1: Jones'reagent / acetone / 6 h 2: 92 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 3: 90 percent / LiBr, Li2CO3 / dimethylformamide / 0.75 h / Heating 4: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1 h, RT, 2b) 30 min, reflux View Scheme

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

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

1: 90 percent / LiBr, Li2CO3 / dimethylformamide / 0.75 h / Heating 2: 1) ozone, 2) water / ethanol, 1) - 80 deg C, 4 h, 2a) 1 h, RT, 2b) 30 min, reflux View Scheme

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

1: lithium alanate; diethyl ether 2: MnO2; acetone View Scheme

manganese(IV) oxide; acetone

water; ozone ethanol, 1) - 80 deg C, 4 h, 2a) 1 h, RT, 2b) 30 min, reflux; Yield given. Multistep reaction;