1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / |Inert atmosphere 3.1: dichloromethane / 1 h / 20 °C / |Inert atmosphere 4.1: triethylamine; methanol / dichloromethane / 4 h / 20 °C / |Inert atmosphere 5.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.17 h / -78 - 0 °C / |Inert atmosphere 6.1: dichloromethane / 2 h / 20 °C / |Inert atmosphere 7.1: zinc; acetic acid / 2.08 h / 0 - 20 °C / |Inert atmosphere 8.1: acetic acid; sodium cyanoborohydride / ethanol / |Reflux; |Inert atmosphere 9.1: sodium hydrogencarbonate / dichloromethane; water / 20 °C 10.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / |Reflux; |Inert atmosphere 11.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 12.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 13.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 15.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 16.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 17.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 18.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 19.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 19.2: 0.5 h / 50 °C / |Inert atmosphere 20.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

1.1: dichloromethane / 1 h / 20 °C / |Inert atmosphere 2.1: triethylamine; methanol / dichloromethane / 4 h / 20 °C / |Inert atmosphere 3.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.17 h / -78 - 0 °C / |Inert atmosphere 4.1: dichloromethane / 2 h / 20 °C / |Inert atmosphere 5.1: zinc; acetic acid / 2.08 h / 0 - 20 °C / |Inert atmosphere 6.1: acetic acid; sodium cyanoborohydride / ethanol / |Reflux; |Inert atmosphere 7.1: sodium hydrogencarbonate / dichloromethane; water / 20 °C 8.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / |Reflux; |Inert atmosphere 9.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 10.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 11.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 13.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 14.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 15.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 16.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 17.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 17.2: 0.5 h / 50 °C / |Inert atmosphere 18.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

1.1: 55.7 percent / tetrahydrofuran / 24 h / 20 °C 2.1: aq. HCl / 1 h / 37 °C 3.1: 0.758 g / LiBr; TEA / CHCl3 / 12 h / 0 - 5 °C 4.1: (-)-dibenzoyl-L-tartaric acid / acetonitrile; H2O / 60 °C 4.2: 226 mg / NaOH / CHCl3; H2O / pH 9 5.1: 77 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 6.1: NaOMe / methanol / 0.5 h / Heating 6.2: HCl / 0.75 h / Heating View Scheme

1.1: 0.758 g / LiBr; TEA / CHCl3 / 12 h / 0 - 5 °C 2.1: (-)-dibenzoyl-L-tartaric acid / acetonitrile; H2O / 60 °C 2.2: 226 mg / NaOH / CHCl3; H2O / pH 9 3.1: 77 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 4.1: NaOMe / methanol / 0.5 h / Heating 4.2: HCl / 0.75 h / Heating View Scheme

1.1: aq. HCl / 1 h / 37 °C 2.1: 0.758 g / LiBr; TEA / CHCl3 / 12 h / 0 - 5 °C 3.1: (-)-dibenzoyl-L-tartaric acid / acetonitrile; H2O / 60 °C 3.2: 226 mg / NaOH / CHCl3; H2O / pH 9 4.1: 77 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 5.1: NaOMe / methanol / 0.5 h / Heating 5.2: HCl / 0.75 h / Heating View Scheme

1.1: 80 percent / methylamine / benzene / 1 h / 10 - 15 °C 2.1: aq. HCl / 1 h / 37 °C 3.1: 0.758 g / LiBr; TEA / CHCl3 / 12 h / 0 - 5 °C 4.1: (-)-dibenzoyl-L-tartaric acid / acetonitrile; H2O / 60 °C 4.2: 226 mg / NaOH / CHCl3; H2O / pH 9 5.1: 77 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 6.1: NaOMe / methanol / 0.5 h / Heating 6.2: HCl / 0.75 h / Heating View Scheme

1.1: 77 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 2.1: NaOMe / methanol / 0.5 h / Heating 2.2: HCl / 0.75 h / Heating View Scheme

1.1: (-)-dibenzoyl-L-tartaric acid / acetonitrile; H2O / 60 °C 1.2: 226 mg / NaOH / CHCl3; H2O / pH 9 2.1: 77 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 3.1: NaOMe / methanol / 0.5 h / Heating 3.2: HCl / 0.75 h / Heating View Scheme

1.1: 35 percent / toluene / 48 h / 20 °C 2.1: 80 percent / methylamine / benzene / 1 h / 10 - 15 °C 3.1: aq. HCl / 1 h / 37 °C 4.1: 0.758 g / LiBr; TEA / CHCl3 / 12 h / 0 - 5 °C 5.1: (-)-dibenzoyl-L-tartaric acid / acetonitrile; H2O / 60 °C 5.2: 226 mg / NaOH / CHCl3; H2O / pH 9 6.1: 77 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 7.1: NaOMe / methanol / 0.5 h / Heating 7.2: HCl / 0.75 h / Heating View Scheme

1: methyl (6aR,9S)-4,7-ditosyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylate in tetrahydrofuran T=-78°C; 0.1 h; Inert atmosphere; 2: formaldehyd With sodium cyanoborohydride; acetic acid in methanol; water T=20°C; 2 h; optical yield given as percent de;