1: 2.) 4-(dimethylamino)pyridine, trimethylamine / 1.) ether, THF, 10 min, 2.) CH2Cl2, 0 deg C, 30 min, 3.) CH2Cl2, 10 min, r. t. 2: 100 percent / N-bromosuccinimide, DMSO / tetrahydrofuran / 6 h / 0 °C 3: 79 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / toluene / 4 h / 120 °C 4: 87 percent / pyridinium dichromate, 3A molecular sieves / CH2Cl2 / 4 h / Ambient temperature 5: 1.) 5 N sodium hydroxide, 2.) p-toluenesulfonic acid / 1.) THF, H2O, 26 h, r. t., 2.) aq. EtOH, 60 - 65 deg C, 24 h 6: 74 percent / xylene / 36 h / 210 °C 7: 94 percent / lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 3.5 h / Ambient temperature View Scheme

1.1: 99 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 2482.38 Torr 2.1: 82 percent / LiAlH4 / diethyl ether / 24 h / Heating 3.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 4.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 5.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 6.1: 100 percent / K2CO3 / methanol / 1.5 h / 20 °C 7.1: 100 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - -40 °C 8.1: 90 percent / NaOMe / methanol / 20 °C 9.1: 93 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C 10.1: 95 percent / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C 11.1: CDI / tetrahydrofuran / 3 h / 20 °C 11.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 12.1: CDI / tetrahydrofuran / 3 h / 20 °C 12.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 13.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 14.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 14.2: 62 percent / benzene; CHCl3 / Heating 15.1: 65 percent / MgBr2*OEt2 / benzene; diethyl ether / 11 h / 0 - 20 °C View Scheme

1: aq. NaOH solution 2: methanol; acetone; diethyl ether View Scheme

hydrogenchloride; acetone

1: ethanol; sodium acetate 2: acetone; aqueous hydrochloric acid View Scheme

1.1: sodium carbonate / Hermann's catalyst / ethanol / 15 h / Reflux 2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane; water / 4 h / 20 °C 2.2: 1 h / 20 °C 3.1: sodium tetrahydroborate; methanol / 0 - 20 °C View Scheme

methanol; diethyl ether; acetone

sodium hydroxide

sodium hydroxide

1.1: 100 percent / DMAP / pyridine / 16 h / 20 °C 2.1: 66 percent / PPL / dimethylsulfoxide; aq. phosphate buffer / 2.5 h / 20 °C / pH 7.8 3.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C 4.1: 100 percent / K2CO3 / methanol / 1.5 h / 20 °C 5.1: 100 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - -40 °C 6.1: 90 percent / NaOMe / methanol / 20 °C 7.1: 93 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C 8.1: 95 percent / 2-methyl-2-butene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C 9.1: CDI / tetrahydrofuran / 3 h / 20 °C 9.2: 20 percent / KHMDS / tetrahydrofuran; toluene / 7 h / 0 - 20 °C 10.1: CDI / tetrahydrofuran / 3 h / 20 °C 10.2: 64 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 11.1: 85 percent / CuCN / tetrahydrofuran / 3.5 h / 10 °C 12.1: TBAF / tetrahydrofuran / 5 h / 40 - 50 °C 12.2: 62 percent / benzene; CHCl3 / Heating 13.1: 65 percent / MgBr2*OEt2 / benzene; diethyl ether / 11 h / 0 - 20 °C View Scheme