(i) EtOH, (ii) NaBH4; Multistep reaction;

1: 93 percent / TiCl4, Zn, pyridine / tetrahydrofuran / 2 h / Heating 2: OsCl3, dihydroquinidine 4-chlorobenzoate, N-methylmorpholine N-oxide / acetone; H2O / 24 h / Ambient temperature 3: SOCl2, Et3N / diethyl ether / 1 h / 0 deg C to r.t. 4: RuCl3, NaOCl / acetonitrile 5: 2 h / r.t. to 130 deg C 6: 85 percent / NaOAc / xylene / 2 h / Heating 7: 87 percent / aq. HCl / acetone / 0 deg C to r.t. 8: 85 percent / NaOAc / xylene / 2 h / Heating 9: 88 percent / H2 / 10percent Pd/C / propan-2-ol; H2O / 38000 Torr View Scheme

1.1: potassium hydroxide / methanol; N,N-dimethyl-formamide / 2.5 h / -10 °C / Inert atmosphere 2.1: sodium tetrahydroborate; diphenyl diselenide; sodium hydroxide / ethanol / 18 h / 40 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 20 °C / Inert atmosphere 4.1: sodium hydroxide / chloroform / 0 - 20 °C 5.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere 5.2: 20 °C / Inert atmosphere; Cooling with ice 6.1: palladium 10 on activated carbon; hydrogen; acetic acid / methanol / 16 h 7.1: berberine bridge enzyme; tris(hydroxymethyl)methylamine hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction View Scheme

1: With 3-chloro-benzenecarboperoxoic acid in dichloromethane T=0°C; 2 h; 2: With ammonia in methanol T=20°C;

1: 93 percent / sodium chlorite; sulfamic acid; acetic acid / H2O / 1 h / 20 °C 2: 94 percent / thionyl chloride / toluene / 6 h / 100 °C View Scheme

trimethyl orthoformate in 1,2-dichloro-ethane T=20°C; 2 h;

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 2: sodium hydroxide / methanol; water / 0.08 h / 20 °C 3: N-bromosuccinmide / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere View Scheme

phthalic anhydride; hydroxylamine hydrochloride; triethylamine in acetonitrile 7 h; Heating;