1: aqueous KOH 2: acetyl chloride 3: palladium; chloroform / Hydrogenation View Scheme

1: aqueous KOH 2: palladium; methanol / Hydrogenation View Scheme

1: 1) SnCl4, 2) 1 M HCl / 1) -10 deg C, 3 h, 2) MeOH, reflux, 2 h 2: 90 percent / ethanol / 4 h / Heating 3: 1) catecholborane, 2) AcONa, H2O / 1) CH2Cl2, 5 deg C, 2) toluene, reflux, 3 h 5: 1) nBuLi, 2) HCl / 1) THF, - 78 deg C 6: BH3, pyridine / trifluoroacetic acid / 2 h / Ambient temperature 7: 10percent aq. NaOH / Ambient temperature 8: 3 h / Ambient temperature 9: 4-N,N-dimethylaminopyridine / pyridine / 24 h / Ambient temperature 10: 10percent Pd/C / cyclohexane / 1 h / Heating 11: 1) (CF3CO)2O, CF3COOH, 2) MeOH / 1) 0 deg C, 1 h 12: 90 percent / SO3, NEt3 / dimethylsulfoxide 13: 40 percent / AlCl3, air / nitrobenzene View Scheme