1.1: POCl3 / 0.75 h / 35 °C 1.2: 99 percent / aq. NaOH / dimethylformamide / 0.17 h / Heating 2.1: 99 percent / NH4OAc / 1 h / Heating 3.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4.1: ethanol / 25 °C 4.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 5.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 6.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 7.1: 96 percent / EDCI; DMAP / CH2Cl2 / 16 h / 0 - 25 °C 8.1: 53 percent / various solvent(s) / 90 h / 230 °C 9.1: Chiracel OD / propan-2-ol; hexane 10.1: LDA; bis(trimethylsilyl)peroxide / tetrahydrofuran / 4 h / -40 °C 10.2: 64 percent / tetrahydrofuran / 2 h / -40 - 20 °C 11.1: 70 percent / Lawesson's reagent / toluene / 3 h / 110 °C 12.1: 91 percent / Raney-Ni; H2 / tetrahydrofuran / 15 h / 20 °C 13.1: 97 percent / NaOAc / 17 h / 20 °C 14.1: 98 percent / H2 / PtO2 / methanol; ethyl acetate / 3 h / 2068.59 - 2327.17 Torr 15.1: 89 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C 16.1: 75 percent / DEAD; PPh3 / tetrahydrofuran / 24 h / 20 °C View Scheme

1.1: POCl3 / 0.75 h / 35 °C 1.2: 99 percent / aq. NaOH / dimethylformamide / 0.17 h / Heating 2.1: 99 percent / NH4OAc / 1 h / Heating 3.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4.1: ethanol / 25 °C 4.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 5.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 6.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 7.1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 8.1: 99 percent / various solvent(s) / 20 h / 230 °C 9.1: Chiracel OD / propan-2-ol; hexane 10.1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 11.1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 12.1: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 13.1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 14.1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 15.1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 16.1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 17.1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 18.1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 19.1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme

1: With trichlorophosphate T=35°C; 0.75 h; 2: With sodium hydroxide in N,N-dimethyl-formamide 0.166667 h; Heating;

1: 6-methoxy-1H-indole With sodium hydride in N,N-dimethyl-formamide T=0°C; 2: methyl iodide in N,N-dimethyl-formamide T=0 - 20°C;

triethyl borane; oxygen; N-ethylpiperidinium hypophosphite in 1,4-dioxane; hexane T=73°C; 2 h; Air atmosphere;

in tetrahydrofuran

tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine in N,N-dimethyl-formamide T=100°C; Inert atmosphere;

1: sodium cyanoborohydride; acetic acid / water; acetonitrile / 12 h / 20 °C 2: triethyl borane; oxygen; N-ethylpiperidinium hypophosphite / 1,4-dioxane; hexane / 2 h / 73 °C / Air atmosphere View Scheme

ammonia; sodium amide und Behandeln des Reaktionsgemisches mit Methyljodid.;

caesium acetate in N,N-dimethyl-formamide T=120°C; 24 h;