potassium carbonate in N,N-dimethyl-formamide T=60°C; 27 h;

palladium 10 on activated carbon; hydrogen in methanol 8 h;

lithium aluminium tetrahydride in tetrahydrofuran

1: 1.) AlCl3, 2.) 28percent NH4OH / 1.) CS2, 0 deg C, 2.) EtOH 2: 57 percent / HCl / Heating 3: 1.) MCPBA, 2.) 10 N KOH / 1.) CH2Cl2, reflux, 18 h 4: 1.) KOH, 2.) HCl 5: 80 percent / EDCl, DMAP / CH2Cl2 6: BBr3 / CH2Cl2 / Ambient temperature 7: 1.) APTS, 2.) Et3N / 1.) reflux 8: 1.) H2, 2.) LiAlH4 / 1.) Pd/C / 1.) MeOH, 2.) Et2O, reflux View Scheme

1: 80 percent / EDCl, DMAP / CH2Cl2 2: BBr3 / CH2Cl2 / Ambient temperature 3: 1.) APTS, 2.) Et3N / 1.) reflux 4: 1.) H2, 2.) LiAlH4 / 1.) Pd/C / 1.) MeOH, 2.) Et2O, reflux View Scheme

1: 57 percent / HCl / Heating 2: 1.) MCPBA, 2.) 10 N KOH / 1.) CH2Cl2, reflux, 18 h 3: 1.) KOH, 2.) HCl 4: 80 percent / EDCl, DMAP / CH2Cl2 5: BBr3 / CH2Cl2 / Ambient temperature 6: 1.) APTS, 2.) Et3N / 1.) reflux 7: 1.) H2, 2.) LiAlH4 / 1.) Pd/C / 1.) MeOH, 2.) Et2O, reflux View Scheme

1: 1.) MCPBA, 2.) 10 N KOH / 1.) CH2Cl2, reflux, 18 h 2: 1.) KOH, 2.) HCl 3: 80 percent / EDCl, DMAP / CH2Cl2 4: BBr3 / CH2Cl2 / Ambient temperature 5: 1.) APTS, 2.) Et3N / 1.) reflux 6: 1.) H2, 2.) LiAlH4 / 1.) Pd/C / 1.) MeOH, 2.) Et2O, reflux View Scheme

1: 1.) KOH, 2.) HCl 2: 80 percent / EDCl, DMAP / CH2Cl2 3: BBr3 / CH2Cl2 / Ambient temperature 4: 1.) APTS, 2.) Et3N / 1.) reflux 5: 1.) H2, 2.) LiAlH4 / 1.) Pd/C / 1.) MeOH, 2.) Et2O, reflux View Scheme

2: NaIO4 / methanol; H2O 3: NaBH4 / methanol; H2O View Scheme

1: 78.2 percent / K2CO3 / butan-2-one / 16 h / Heating 2: 83.4 percent / diisobutyl aluminum hydride / diethyl ether; hexane / -20 °C 3: 1.) Ti(i-PrO)4, (+)-diethyl tartrate, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -20 deg C, 2.) CH2Cl2, -20 deg C, overnight 4: 88 percent / pyridine / 16 h / 5 °C 5: H2 / 10percent Pd/C / methanol / 6 h / 2585.7 Torr 6: 10percent aq. KOH / methanol / 0.5 h / Ambient temperature 7: 2 h / Heating 8: 1.) NaIO4, 2.) NaBH4 / 1.) ethanol, water, 10 min, 2.) ethanol, water, 10 min View Scheme