1: 82 percent / xylene / 18 h / Heating 2: 81 percent / I2 / tetrahydrofuran; H2O / 0 °C 3: 86 percent / NaBH4 / ethanol 4: 93 percent / imidazole / dimethylformamide 5: 94 percent / xylene / 7 h / Heating 6: 81 percent / tetrahydrofuran / -78 °C 7: 85 percent / N-Methylmorpholine-N-oxide, OsO4 8: 93 percent / anhydr. CuSO4, TsOH 9: 75 percent / tetrahydrofuran / 24 h / Ambient temperature 10: 87 percent / Bu4NF / tetrahydrofuran / 4 h / Ambient temperature 11: 80 percent / PCC,molecular sieve / CH2Cl2 / 1 h / Ambient temperature 12: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min. 13: 50percent aq. AcOH / 72 h / Ambient temperature View Scheme

1: 91 percent / MeONa / methanol 2: acetic acid / ethyl acetate 3: 200 °C View Scheme

1: 86 percent / H2, Et3N / Pd 2: 91 percent / MeONa / methanol 3: acetic acid / ethyl acetate 4: 200 °C View Scheme

orthoformic acid triethyl ester; acetic acid 1.) EtOAc 2.) 250 deg C; Yield given. Multistep reaction;

1: HBr, Ac2O 2: 1.) Hydrogen, Et3N 2.) MeONa / 2.) MeOH 3: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C View Scheme

T=200°C; Yield given;

in xylene 18 h; Heating;

1: 82 percent / xylene / 18 h / Heating 2: 81 percent / I2 / tetrahydrofuran; H2O / 0 °C 3: 86 percent / NaBH4 / ethanol View Scheme

1: 82 percent / xylene / 18 h / Heating 2: 81 percent / I2 / tetrahydrofuran; H2O / 0 °C 3: 86 percent / NaBH4 / ethanol 4: 93 percent / imidazole / dimethylformamide View Scheme

1: 82 percent / xylene / 18 h / Heating 2: 81 percent / I2 / tetrahydrofuran; H2O / 0 °C 3: 86 percent / NaBH4 / ethanol 4: 93 percent / imidazole / dimethylformamide 5: 94 percent / xylene / 7 h / Heating 6: 81 percent / tetrahydrofuran / -78 °C 7: 85 percent / N-Methylmorpholine-N-oxide, OsO4 8: 93 percent / anhydr. CuSO4, TsOH 9: 75 percent / tetrahydrofuran / 24 h / Ambient temperature 10: 87 percent / Bu4NF / tetrahydrofuran / 4 h / Ambient temperature 11: 80 percent / PCC,molecular sieve / CH2Cl2 / 1 h / Ambient temperature 12: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min. 13: 50percent aq. AcOH / 72 h / Ambient temperature View Scheme