1: 1.) n-BuLi / 1.) THF, room temperature, 30 min, 2.) -78 deg C, 1.5 h 2: 1.) MeSO2X, 2.) potassium superoxide, 18-crown-6 / 2.) DMF, DMSO 3: 3.4 g / H2 / Lindlar catalyst / diethyl ether; ethanol / 3 h 4: 85 percent / 70percent t-butyl hydroperoxide, vanadyloxy acetylacetonate / benzene / 2.5 h / Ambient temperature 5: 1.)Et3Al, 2.) 2M HCl / 1.) THF, hexane, 0 deg C, 16 h, 2.) MeOH, THF, room temperature, 1 h 6: 56 percent / toluene-p-sulphonic acid / 17 h / Ambient temperature 7: 65 percent / di-isobitylaluminium hydride / tetrahydrofuran; hexane / 5 h / Ambient temperature 8: 580 mg / pyridine / 16 h / Ambient temperature 9: NaBH4 / methanol; tetrahydrofuran / 3 h / Ambient temperature 10: 260 mg / pyridine / 3 h / Ambient temperature 11: 96 percent / NaI / acetone / 72 h / Heating 12: 98 percent / Bu3SnH / tetrahydrofuran / 18 h / Ambient temperature 13: 396 mg / 5percent KOH-MeOH / tetrahydrofuran / 1 h / Ambient temperature 14: pyridine / 2 h / Ambient temperature 15: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 16: 209 mg / LiBr / dimethylformamide / 1 h / Heating 17: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 18: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

1: 38 percent / tetrahydrofuran / -78 °C 2: H2 / Pd/C (5percent) / ethyl acetate View Scheme

(i) Mg, THF, (ii) /BRN= 4205826/, THF, (iii) aq. HCl, MeOH; Multistep reaction;