1.1: 93 percent / TiCl4 2.1: m-CPBA; TsOH / CH2Cl2 / 20 °C 3.1: K2CO3 / CH2Cl2; methanol 4.1: 60 percent / acetic acid / Heating 5.1: 97 percent / K2CO3; Br2 / CH2Cl2 / 1 h / 0 °C 6.1: 94 percent / diisopropylethylamine / dimethylformamide / 1.5 h / 20 °C 7.1: 77 percent / i-PrOTMS; TMSOTf / CH2Cl2 / -78 °C 8.1: 85 percent / tetrahydrofuran / 24 h / Heating 9.1: 85 percent / Me2AlCl / CH2Cl2 / 0.17 h / -78 °C 10.1: LHMDS / tetrahydrofuran; hexane / 1.5 h / -78 - -10 °C 10.2: 70 percent / tetrahydrofuran; hexane / 3 h / -20 - 0 °C 11.1: 81 percent / NaBH4 / ethanol / 2.5 h / -78 °C 12.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / -10 °C 13.1: n-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C 13.2: BF3*Et2O / tetrahydrofuran; pentane / 3 h / -78 °C 14.1: 57 percent / second generation Grubbs' catalyst / CH2Cl2 / 48 h / 50 - 55 °C 15.1: 89 percent / 2,6-lutidine; DMAP / pyridine / 1 h / 0 - 20 °C 16.1: 78 percent / pyridine; OsO4 / tetrahydrofuran / 5 h / 0 °C 17.1: 95 percent / pyridine / CH2Cl2 / 2 h / 0 °C 18.1: 84 percent / BnNMe3OH / methanol; tetrahydrofuran / 1 h / 0 °C 19.1: n-BuLi; WCl6 / tetrahydrofuran; hexane / 0 - 20 °C 20.1: 12 mg / pyridinum p-toluenesulfonate / methanol / 6 h / 0 °C 21.1: 69 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0 - 20 °C 22.1: 40 percent / aq. HF / acetonitrile / 0 - 20 °C View Scheme

LiSEt in N,N-dimethyl-formamide T=150°C; 0.333333 h; Inert atmosphereMicrowave irradiation;

1: 87 percent / HNO3 / 0 °C 2: 97 percent / H2 / 5 percent Pd-C / ethanol View Scheme

titanium tetrachloride in benzene T=0°C; Friedel-Crafts acylation; 0.5 h;

1.1: 90 percent / POCl3 / 60 °C 2.1: 94 percent / Cu(NO3)2*3H2O 3.1: H2 / Raney Nickel / tetrahydrofuran; H2O / 20 °C 4.1: 92 percent / NBS / CHCl3 / 0.08 h / 20 °C 5.1: HCl; NaNO2 / tetrahydrofuran; H2O 5.2: 89 percent / urea; H3PO2 / tetrahydrofuran; H2O 6.1: 87 percent / PCC / CH2Cl2 / 0 - 20 °C 7.1: 94 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

1: 93 percent / TiCl4 2: m-CPBA; TsOH / CH2Cl2 / 20 °C 3: K2CO3 / CH2Cl2; methanol 4: 60 percent / acetic acid / Heating View Scheme

Multistep reaction;

aluminium trichloride in diethyl ether 4 h;

1: dioxane*Br2 2: NaNH2 / liquid ammonia 3: (i) aq. HBr, NaNO2, (ii) CuBr, aq. HBr 4: aq. KMnO4, Py View Scheme

1: 94 percent / Claycop; Ac2O / diethyl ether / 1 h / 20 °C 2: 96 percent / AlCl3 / CH2Cl2 / 21 h / 20 °C View Scheme