1: 96 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / 2 °C 2: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h 3: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight 4: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature 5: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature 6: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 7: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

1: 64 percent / Pd(PPh3)4 (3percent) / acetonitrile; dimethylsulfoxide / 12 h / 20 °C 2: 95 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr 3: 95 percent / NaOH / methanol; H2O 4: 95 percent / EtO2C-N=N-CO2Et, ZnCl2, PBu3 / 3 h / 20 °C 5: 90 percent / K2CO3 / methanol / 1 h / 20 °C 6: 81 percent / Na / NH3 View Scheme

1: 77 percent / acetonitrile; dimethylsulfoxide / 3 h / 80 °C 2: 98 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr 3: 99 percent / NaOH / methanol; H2O 4: 100 percent / Et3N / tetrahydrofuran 5: 97 percent / K2CO3 / methanol / 1 h / 20 °C 6: 77 percent / Na / liquid ammonia 7: 91 percent / NaBH4 View Scheme

1: 64 percent / Pd(PPh3)4 (3percent) / acetonitrile; dimethylsulfoxide / 12 h / 20 °C 2: 95 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr 3: 95 percent / NaOH / methanol; H2O 4: 95 percent / EtO2C-N=N-CO2Et, ZnCl2, PBu3 / 3 h / 20 °C 5: 90 percent / K2CO3 / methanol / 1 h / 20 °C 6: 81 percent / Na / NH3 7: 95 percent / NaBH4 View Scheme

1: NaH, PPh3 / Pd(OAc)2 / tetrahydrofuran / 3.5 h 2: 1.) dppe, triethylamine, 2.) p-aminothiophenol, Cs2CO3 / 1.) Pd(dba)2 / 1.) toluene, reflux, 6 min, 2.) DMF, 85 deg C, 15 min 3: 98 percent / aq. KOH / methanol / 0.17 h / 50 °C 4: 21 percent / p-benzoquinone, LiOAc*2H2O / Pd(OAc)2 / acetone / 48 h / 40 °C View Scheme

Multi-step reaction with 5 steps 1: 77 percent / acetonitrile; dimethylsulfoxide / 3 h / 80 °C2: 98 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr3: 99 percent / NaOH / methanol; H2O4: 100 percent / Et3N / tetrahydrofuran5: 97 percent / K2CO3 / methanol / 1 h / 20 °C  

Multi-step reaction with 5 steps 1: 64 percent / Pd(PPh3)4 (3percent) / acetonitrile; dimethylsulfoxide / 12 h / 20 °C2: 95 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr3: 95 percent / NaOH / methanol; H2O4: 95 percent / EtO2C-N=N-CO2Et, ZnCl2, PBu3 / 3 h / 20 °C5: 90 percent / K2CO3 / methanol / 1 h / 20 °C  

 in  dimethyl sulfoxide T=80°C; 3 h;