1: 88 percent / Rh(acac)(C2H4)2; (R)-Segphos / dioxane; H2O / 8 h / 60 °C 2: 95 percent / diisobutylaluminum hydride / toluene; hexane / 2.5 h / -25 - -20 °C 3: 91 percent / H2 / Pd/C / methanol / 12 h / 2585.74 Torr / Heating View Scheme

sodium hydroxide in methanol 4 h; Heating;

1: 83 percent / Et3N; DMAP / CH2Cl2 / 0 - 20 °C 2: 81 percent / K2CO3 / acetonitrile / 48 h / 60 °C 3: 97 percent / H2 / 10 percent Pd/C / methanol / 12 h / 20 °C / 760 Torr View Scheme

1: 81 percent / K2CO3 / acetonitrile / 48 h / 60 °C 2: 97 percent / H2 / 10 percent Pd/C / methanol / 12 h / 20 °C / 760 Torr View Scheme

1: 1.) Mg, 2.) CuBr*Me2S, Me2S / 1) THF, reflux, 15 min; 2) THF, -50 deg C, 3 min; 3) THF, 10 deg C, 2 h 2: 90 percent / LiOH, H2O2 / tetrahydrofuran; H2O 3: 1.) SOCl2 / 1) benzene, 50 deg C, 50 min; 2) ether, rt, 1.5 h 4: 1.) LiAlH4, 2.) H2 / 2.) Pd/C / 1) ether, rt, overnight; 2) MeOH, 1 atm, rt, overnight View Scheme

1: 1.) Mg, 2.) CuBr*Me2S, Me2S / 1) THF, reflux, 15 min; 2) THF, -50 deg C, 3 min; 3) THF, 10 deg C, 2 h 2: 90 percent / LiOH, H2O2 / tetrahydrofuran; H2O 3: 1.) SOCl2 / 1) benzene, 50 deg C, 50 min; 2) ether, rt, 1.5 h 4: 1.) LiAlH4, 2.) H2 / 2.) Pd/C / 1) ether, rt, overnight; 2) MeOH, 1 atm, rt, overnight View Scheme

1: 90 percent / LiOH, H2O2 / tetrahydrofuran; H2O 2: 1.) SOCl2 / 1) benzene, 50 deg C, 50 min; 2) ether, rt, 1.5 h 3: 1.) LiAlH4, 2.) H2 / 2.) Pd/C / 1) ether, rt, overnight; 2) MeOH, 1 atm, rt, overnight View Scheme

hydrogen bromide; acetic acid

1.1: potassium carbonate 2.1: |Inert atmosphere; |Schlenk technique 3.1: triethylamine / toluene / 2 h / 150 °C / |Inert atmosphere 4.1: sec.-butyllithium / diethyl ether; cyclohexane; hexane / 1 h / -78 °C / |Inert atmosphere; |Schlenk technique 4.2: 2 h / -78 °C / |Inert atmosphere; |Schlenk technique 4.3: 16.08 h / -78 - 20 °C / |Inert atmosphere; |Schlenk technique 5.1: tetrabutyl ammonium fluoride; water / toluene / 1.5 h / 20 °C 6.1: osmium(VIII) oxide; sodium periodate 7.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 8.1: hydrogen bromide; acetic acid View Scheme

1.1: calcium carbonate; palladium diacetate / methanol / 4 h / 60 °C 1.2: 20 °C 2.1: copper diacetate; DEMS; josiphos / tetrahydrofuran; toluene; tert-butyl alcohol / 3 h / 20 °C / |Inert atmosphere 3.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 72 h / 20 °C / |Inert atmosphere View Scheme